1H NMR determination of adulteration of anabolic steroids in seized drugs.

Abstract:

:Counterfeiting and adulteration of pharmaceuticals is a prevalent problem worldwide and represents a major health risk to the population, with anabolic steroids being one of the main classes of drugs consumed and obtained from dubious sources. In this work, we propose the use of the 1H NMR technique to evaluate formulations containing anabolic steroids, with analysis of 40 samples of anabolic drugs that are used in injectable and capsule forms. The samples analyzed presented the following active ingredients: testosterone propionate, testosterone phenylpropionate, testosterone isocaproate, testosterone decanoate, testosterone cypionate, testosterone undecanoate, stanozolol, drostanolone propionate, trenbolone acetate, oxymetholone, and methandrostenolone. The 1H NMR spectroscopic measurements were performed using a 600 MHz Bruker Avance III spectrometer, with deuterated chloroform (CDCl3) containing 0.1% TMS as solvent. Of the 40 samples analyzed, eight did not show the presence of the active principle stated on the label. Three types of adulteration were found in the analyzed samples: absence of the active ingredient, adulteration with other substances, and concentration values below those indicated on the label. Sildenafil citrate was found in four samples. The GC-MS technique was used to confirm the adulteration results found using 1H NMR. Quantitative determination by NMR was performed using internal standard and ERETIC 2 methods, and the results obtained were statistically the same.

journal_name

Steroids

journal_title

Steroids

authors

Ribeiro MVM,Boralle N,Felippe LG,Pezza HR,Pezza L

doi

10.1016/j.steroids.2018.07.002

subject

Has Abstract

pub_date

2018-10-01 00:00:00

pages

47-56

eissn

0039-128X

issn

1878-5867

pii

S0039-128X(18)30118-1

journal_volume

138

pub_type

杂志文章

相关文献

STEROIDS文献大全
  • Steroidal alkenylphosphonates via palladium-catalyzed coupling reactions.

    abstract::The palladium-catalyzed coupling of various 17-iodo-delta 16 steroids (17-iodo-androst-16-ene, 17-iodo-4-methyl-4-aza-androst-16-en-3-one, and 17-iodo-4-aza-androst-16-en-3-one) with dialkyl phosphites (dimethyl phosphite, diethyl phosphite, and diisopropyl phosphite) was examined in detail. The only successful condit...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(95)00121-6

    authors: Skoda-Földes R,Kollár L,Horváth J,Tuba Z

    更新日期:1995-12-01 00:00:00

  • 15 beta-hydroxysteroids (Part III). Steroids of the human perinatal period: the synthesis of 3 beta, 15 beta, 17 alpha-trihydroxy-5-pregnen-20-one. Application of n-butyl boronic acid protection of a 17,20-glycol.

    abstract::We report the synthesis of 3 beta,15 beta,17 alpha-trihydroxy-5-pregnen-20- one (1) from 3 beta,15 beta-dihydroxy-5,16-pregnadien-20-one (11) in 7 steps using boronate derivatives as a means of protecting the 17,20-glycol side-chain of steroid intermediates. 16 alpha,17 alpha-Epoxy-3 beta,15 beta-dihydroxy-5- pregnen-...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(95)00169-q

    authors: Joannou GE,Reeder AY

    更新日期:1996-01-01 00:00:00

  • Prostaglandin inhibitors and the development of mung bean seedlings.

    abstract::The effect of cortisol and prostaglandin inhibitors on the growth and development of germinating mung bean, Vigna radiata L. Wilzek, cv. Jumbo was investigated. Cortisol, indomethacin, and a mixture of cortisol with aspirin, or benoxaprofen significantly increased radicle length and the number of lateral roots as comp...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(85)90052-2

    authors: Gawienowski AM,Csernus KM,Simon JE,Craker LE

    更新日期:1985-08-01 00:00:00

  • The measurement of 4-androstene-3, 11, 17-trione (11-oxo-androstenedione) by radioimmunoassay in human plasma.

    abstract::A radioimmunoassay (RIA) method is described for the determination of 4-androstene-3, 11, 17-trione (11-oxo-androstenedione) in human plasma. 4-androstene-3, 11, 17-trione 3-(0-carboxymethyl) oxime-bovine serum albumin conjugate was used to generate highly specific antiserum in rabbits. Cross reactivities of several o...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(84)80013-6

    authors: Schlaghecke R,Kley HK,Krüskemper HL

    更新日期:1984-07-01 00:00:00

  • Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments.

    abstract::Estradiol benzoate (EB) has been one of the most widely used estrogenic agents in animal husbandry, as a way of exogenously introducing the natural hormone estradiol-17β into the animal organism. Estradiol was previously employed to induce anabolic effects or reproductive improvements in cattle. However, the employmen...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2010.12.005

    authors: Regal P,Nebot C,Díaz-Bao M,Barreiro R,Cepeda A,Fente C

    更新日期:2011-03-01 00:00:00

  • Androgen receptor isoforms AR-A and AR-B display functional differences in cultured human bone cells and genital skin fibroblasts.

    abstract::Two isoforms of the androgen receptor (AR-A and AR-B), differing by a lack of the first 187 amino acids in the NH2-terminal transactivation domain of AR-A, are expressed in connective tissue and bone. Transient transfections of normal human osteoblastic cells (HOB) and of genital skin fibroblasts defective in AR (GSF-...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2003.08.016

    authors: Liegibel UM,Sommer U,Boercsoek I,Hilscher U,Bierhaus A,Schweikert HU,Nawroth P,Kasperk C

    更新日期:2003-12-01 00:00:00

  • From ligand structure to biological activity: modified estratrienes and their estrogenic and antiestrogenic effects in MCF-7 cells.

    abstract::A variety of compounds, including the selective estrogen receptor (ER) modulators tamoxifen and raloxifene, phytoestrogens such as genistein, and xenoestrogens such as bisphenol, bind to the estrogen receptor and elicit biological responses. Structural studies have linked the altered activity of compounds such as 4-hy...

    journal_title:Steroids

    pub_type: 杂志文章,评审

    doi:10.1016/j.steroids.2004.03.014

    authors: Brooks SC,Skafar DF

    更新日期:2004-06-01 00:00:00

  • An expeditious synthesis of spinasterol and schottenol, two phytosterols present in argan oil and in cactus pear seed oil, and evaluation of their biological activities on cells of the central nervous system.

    abstract::Spinasterol and schottenol, two phytosterols present in argan oil and in cactus pear seed oil, were synthesized from commercially available stigmasterol by a four steps reactions. In addition, the effects of these phytosterols on cell growth and mitochondrial activity were evaluated on 158N murine oligodendrocytes, C6...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2015.01.005

    authors: Badreddine A,Karym el M,Zarrouk A,Nury T,El Kharrassi Y,Nasser B,Cherkaoui Malki M,Lizard G,Samadi M

    更新日期:2015-07-01 00:00:00

  • Blood pressure changes following chronic administration to rats of 3beta,16beta-dihydroxy-5-androsten-17-one, 3beta,17beta-dihydroxy-5-androsten-16-one and 21-hydroxy-4-pregnene-3,20-dione-21-acetate.

    abstract::The urinary excretion of 3beta,16beta-dihydroxy-5-androsten-17-one (16beta-OH-DHEA) is increased in patients with low renin essential hypertension. This steroid and its isomer 3beta,17beta-dihydroxy-5-androsten-16-one (16-oxo-A) have also been reported to have mineralocorticoid activity in adrenalectomized rats. These...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(77)90105-2

    authors: Ogihara T,Ichihara K,Yamamoto T,Kumahara Y,Kircher HW,Nugent CA

    更新日期:1977-01-01 00:00:00

  • Antigen-specific T cell functions are suppressed over the estrogen-dendritic cell-indoleamine 2,3-dioxygenase axis.

    abstract::Estrogen results in the suppression of experimental allergic encephalomyelitis (EAE), a frequently used experimental animal model of multiple sclerosis (MS). The mechanism by which estrogen acts in diseases with an autoimmune background is less clear. Here, we used splenic dendritic cells (DC) from the Lewis rats EAE ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2004.05.019

    authors: Xiao BG,Liu X,Link H

    更新日期:2004-09-01 00:00:00

  • Synthesis and biological activities of 2 beta-chloro-, 2 beta-fluoro-, and 2 beta-methoxy-1 alpha,25-dihydroxyvitamin D3.

    abstract::Using 1 alpha,2 alpha-oxido-cholesta-5,7-diene-3 beta,25-diol (2) as a starting material, the provitamins of calcitriol with an additional 2 beta-chloro-, 2 beta-fluoro-, and 2 beta-methoxy-substituent (3,4,5) are obtained by transdiaxial opening of the oxirane ring with nucleophiles. An efficient irradiation process ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(98)00072-5

    authors: Scheddin D,Mayer H,Schönecker B,Gliesing S,Reichenbächer M

    更新日期:1998-12-01 00:00:00

  • An enzyme immunoassay of estrone in swine serum.

    abstract::An enzyme immunoassay for estrone in swine serum was established. For this, beta-galactosidase from E. coli was conjugated through estrone-17 (O-carboxymethyl)oxime using a mixed anhydride reaction. The percentage of immunoreactive estrone-17 (O-carboxymethyl)oxime-beta-galactosidase conjugate was estimated to be abou...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(82)90136-2

    authors: Tamamura F,Nakao T,Tsunoda N,Kawata K

    更新日期:1982-06-01 00:00:00

  • Biological spectrum of two spirolactone derivatives with some observations on anti-fertility activity.

    abstract::Bioassays were conducted to determine various endocrinological properties of two spirolactone derivatives, 4',5'-dihydrospiro-[estr-4-ene-17,2'(3'H)-furan]-3-one (Compound I) and dispiro[cyclopropane-1,6'-estr-4'-ene-17',2"(3"h)-furan]-3'-one (Compound II). They proved to be very potent estrogen antagonists in immatur...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(77)90123-4

    authors: Brooks JR,Steelman SL,Patanelli DJ

    更新日期:1977-06-01 00:00:00

  • High concentrations of conjugated bile acids inhibit bacterial growth of Clostridium perfringens and induce its extracellular cholylglycine hydrolase.

    abstract::To investigate the effects of conjugated bile acid on bacterial growth and cholylglycine hydrolase activity, Clostridium perfringens from human feces was exposed to varying concentrations of taurine- or glycine-conjugated chenodeoxycholic acid. Extracellular enzyme activity was determined by deconjugation of radiolabe...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(94)90062-0

    authors: Kishinaka M,Umeda A,Kuroki S

    更新日期:1994-08-01 00:00:00

  • Elucidation of two new corticosteroids, betamethasone dibutyrate and betamethasone tributyrate.

    abstract::Corticosteroids were used normally as anti-inflammatory drugs. However, in some area certain corticosteroids might be illegally used as growth promoting agent in feed, and as prohibited doping substances in game and sport for human or/and animal performance-enhancing. Synthesized structural similar corticosteroids wer...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2020.108739

    authors: Chen SY,Fang M,Lin YT,Tsai CF,Cheng HF,Wang DY

    更新日期:2021-01-01 00:00:00

  • Individual and cyclic estrogenic profile in women: Structure and variability of the data.

    abstract::The concentration of estrogens in the body fluids of women is highly variable, due to the menstrual cycle, circadian oscillations, and other physiological and pathological causes. To date, only the cyclic fluctuations of the principal estrogens (estradiol and estrone) have been studied, with limited outcome of general...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2019.108432

    authors: Bozzolino C,Vaglio S,Amante E,Alladio E,Gerace E,Salomone A,Vincenti M

    更新日期:2019-10-01 00:00:00

  • Sex hormone binding globulin levels and free progesterone, testosterone and estradiol 17 beta during the annual cycle of the female turtle, Chrysemys picta.

    abstract::Significant changes in % free serum E2, T and P were observed during the annual cycle of the turtle. In contrast no significant changes in SHBG affinity constants (2.29-4.48 x 10(8) M-7) were found and binding capacity for estradiol 17B was between 3.47 and 3.96 x 10(-7) M except in preovulatory animals (2.00 +/- 0.25...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(88)90144-4

    authors: Albert C,Callard IP

    更新日期:1988-10-01 00:00:00

  • Interleukins 1α and 1β as regulators of steroidogenesis in human NCI-H295R adrenocortical cells.

    abstract::Inflammatory cytokines interleukin-1 (IL-1) and tumor necrosis factor-α (TNF-α) regulate the activity of the hypothalamo-pituitary-adrenal (HPA) axis at several levels. Although hypothalamic CRH secretion may be the primary mechanism by which these cytokines activate the HPA axis, IL-1 expression is increased within t...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2011.04.018

    authors: Tkachenko IV,Jääskeläinen T,Jääskeläinen J,Palvimo JJ,Voutilainen R

    更新日期:2011-09-01 00:00:00

  • Characterization of a hepatic protein in nonhuman primates that binds mibolerone but not dihydrotestosterone or methyltrienolone.

    abstract::During our studies of the hepatic androgen receptor in cynomolgus monkeys, tritiated mibolerone +/- a 200-fold excess of unlabeled mibolerone has been used to determine specific binding in cytosol. During time-course studies, high-capacity, unsaturable binding of [3H]mibolerone was noted after short-term incubations (...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(95)00116-8

    authors: Koritnik DR,Marschke KB,Koshy A

    更新日期:1995-11-01 00:00:00

  • Synthesis and analgesic effects of kyotorphin-steroid linkers.

    abstract::Kyotorphin (KTP, H-Tyr-Arg-OH) was covalently bonded with hydrocortisone or estrone to form the corresponding hydrocortisone-21-O-yl-succinyl-Tyr-ArgOH or estrone-3-O-yl-acyl-Tyr-Arg-OH. Their analgesic activities were investigated using the tail flick test. The potency of the two linkers were significantly higher tha...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(01)00112-x

    authors: Wang C,Zhao M,Yang J,Peng S

    更新日期:2001-11-01 00:00:00

  • In vivo androgen retention in mouse kidney.

    abstract::The in vivo retention of 3-H-testosterone, dihydrotestosterone (DHT), 3alpha-androstanediol (3alpha-DIOL), 3beta-DIOL, androstenedione, progesterone and cortisol by renal cytoplasm and nuclei of male and female mice was studied. Testosterone was the major androgen isolated from cytoplasm and nuclei following testoster...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(75)80011-0

    authors: Bullock LP,Bardin CW

    更新日期:1975-01-01 00:00:00

  • New pregnane-type steroidal alkaloids from Sarcocca saligna and their cholinesterase inhibitory activity.

    abstract::Five new steroidal alkaloids, 5,14-dehydro-N(a)-demethylsaracodine [3beta-N(a)-methyl-20S-N(b)-acetyl-N(b)-methylamino-pregn-5,14-diene] (1), 14-dehydro-N(a)-demethylsaracodine [3beta-N(a)-methyl-20S-N(b)-acetyl-N(b)-methylamino-5alpha-pregn-14-ene] (2), 16-dehydrosarcorine [(20S)-20-(N,N-dimethylamino)-3beta-(N(a)-ac...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2004.03.016

    authors: Atta-ur-Rahman,Feroz F,Naeem I,Zaheer-ul-Haq,Nawaz SA,Khan N,Khan MR,Choudhary MI

    更新日期:2004-10-01 00:00:00

  • In human T cells mifepristone antagonizes glucocorticoid non-genomic rapid responses in terms of Na(+)/H(+)-exchange 1 activity, but not ezrin/radixin/moesin phosphorylation.

    abstract::Glucocorticoids (GCs) and progesterone have been employed as immunosuppressive agents during pregnancy for many years. Intracellular acidification by GCs is due to a rapid non-genomic inhibition of membrane Na(+)/H(+)-exchange 1 (NHE1) activity and is followed by immunosuppression of PHA-stimulated proliferation. NHE1...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2016.01.004

    authors: Chien EJ,Hsu CH,Chang VH,Lin EP,Kuo TP,Chien CH,Lin HY

    更新日期:2016-07-01 00:00:00

  • Measurement of cortisol secretion rate by stable isotope methodology following oral administration of 13C-labeled cortisol to a human subject.

    abstract::Plasma concentration measurements of 13C-labeled cortisol ([1,2,4,19-13C(4)]cortisol, cortisol-13C(4)) and its metabolite cortisone-13C(4) were made simultaneously with measurements of endogenous cortisol and cortisone by gas chromatography-mass spectrometry (GC-MS). After administering a small amount (3mg) of cortiso...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(02)00037-5

    authors: Kasuya Y,Yokokawa A,Shibasaki H,Furuta T

    更新日期:2002-08-01 00:00:00

  • Progesterone receptors in endometrial cancer invasion and metastasis: development of a mouse model.

    abstract::Progestagens inhibit growth of endometrial cancer cells in vivo and in vitro, and also are reported to inhibit endometrial cancer cell invasion. The progesterone receptor (PR) isotypes PRA and PRB have different transcriptional activity. There are indications that relative over expression of PRB could lead to developm...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2003.08.002

    authors: Hanekamp EE,Gielen SC,van Oosterhoud SA,Burger CW,Grootegoed JA,Huikeshoven FJ,Blok LJ

    更新日期:2003-11-01 00:00:00

  • Determination of endocrine disruptors and endogenic androgens and estrogens in rat serum by high-performance liquid chromatography-tandem mass spectrometry.

    abstract::To simultaneously measure some targeted endocrine disruptors and several forms of sex hormones in rat serum, an accurate analytical procedure was developed. First, a comparison between a polymeric-based solid-phase extraction (SPE) and a micro-extraction by packed sorbent was performed to choose the optimal method to ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2015.10.011

    authors: Tournier M,Pouech C,Quignot N,Lafay F,Wiest L,Lemazurier E,Cren-Olivé C,Vulliet E

    更新日期:2015-12-01 00:00:00

  • Membrane estrogen receptor signaling impacts the reward circuitry of the female brain to influence motivated behaviors.

    abstract::Within the adult female, estrogen signaling is well-described as an integral component of the physiologically significant hypothalamic-pituitary-gonadal axis. In rodents, the timing of ovulation is intrinsically entwined with the display of sexual receptivity. For decades, the importance of estradiol activating intrac...

    journal_title:Steroids

    pub_type: 杂志文章,评审

    doi:10.1016/j.steroids.2017.11.013

    authors: Tonn Eisinger KR,Larson EB,Boulware MI,Thomas MJ,Mermelstein PG

    更新日期:2018-05-01 00:00:00

  • Synthetic approaches toward total synthesis of 12 beta-methyl- and 12-methylene-19-norpregnanes.

    abstract::The effect of a substituent in the 12-position of progestagens was studied. To this end, various approaches toward the preparation of 12 beta-alkyl- and 12-alkylidenenorpregnanes were investigated. Eventually, the desired compounds 17 beta-hydroxy-12 beta-methyl-18a-homo-19-nor-17 alpha-pregn-4-en-20-yn-3-one (37) and...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(92)90020-a

    authors: Broess AI,van Vliet NP,Groen MB,Hamersma H

    更新日期:1992-11-01 00:00:00

  • The use of 6alpha-and 6beta-carboxymethyl testosterone-bovine serum albumin conjugates in radioimmunoassay for testosterone.

    abstract::The synthesis of 6alpha- and 6beta-testosterone-bovine serum albumin (BSA) conjugates is described. 6beta-Carboxymethyl-4-androstene-3,17-dione was prepared by a route analogous to that described earlier for 6beta-carboxymethyl progesterone. Sodium borohydride reduction of the 3 and 17 keto groups and subsequent selec...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(75)80004-3

    authors: Jones CD,Mason NR

    更新日期:1975-01-01 00:00:00

  • Differential regulation of the bumetanide-sensitive cotransporter (NKCC2) by ovarian hormones.

    abstract::The Na-K-2Cl cotransporter (NKCC2) regulates sodium transport along the thick ascending limb of Henle's loop and is important in control of sodium balance, renal concentrating ability and renin release. To determine if there are sex differences in NKCC2 abundance and/or distribution, and to evaluate the contribution o...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2010.05.014

    authors: Musselman TM,Zhang Z,Masilamani SM

    更新日期:2010-11-01 00:00:00