Trilostane 曲洛斯坦

CAS 13647-35-3 MFCD00199295

化学结构图

13647-35-3
SMILES: C[C@]12CC[C@H]3[C@@H](CC[C@@]45O[C@@H]4C(O)=C(C#N)C[C@]35C)[C@@H]1CC[C@@H]2O

化学属性

Mol. FormulaC20H27NO3
Mol. Weight329.43
Density1.422
Melting Point269
Appearance Solid powder
SolubilitySoluble in DMSO, not in water

别名和识别编码

Chemical NameTrilostane
CAS Number13647-35-3
Synonym (4α,5α,17β)-3,17-dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile (4a,5a,17b)-3,17-Dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile Androstane-2-carbonitrile, 4,5-epoxy-17-hydroxy-3-oxo-, WIN24540; WIN-24540; WIN 24540; Trilostane; DB01108; D-01180; D 01180; Modrastane. Desopan; Modrenal. Win-24540, Desopan, Modrastane, Modrenal
MDL NumberMFCD00199295
EC Number237-133-0
Beilstein Registry Number2384789
Chemical Name Translation曲洛斯坦
Wiswesser Line NotationT E5 D6663 1A R AX PV RO QHTTTT&J HQ I1 M1 OCN
FormulaC20H27NO3
IUPAC Name(1aR,4aR,4bS,6aS,7S,9aS,9bS,11aS)-2,7-dihydroxy-4a,6a-dimethyl-1a,4,4a,4b,5,6,6a,7,8,9,9a,9b,10,11-tetradecahydrocyclopenta[7,8]phenanthro[1,10a-b]oxirene-3-carbonitrile.
InChIKeyKVJXBPDAXMEYOA-CXANFOAXSA-N
InChIInChI=1S/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3/t12-,13-,14-,15-,17+,18-,19+,20+/m0/s1
Canonical SMILESN#CC1=C(O)[C@@]2([H])O[C@@]23[C@]([C@@]4([H])CC[C@@]5(C)[C@](CC[C@@H]5O)([H])[C@]4([H])CC3)(C)C1
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分类

  • Androgen, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Corticosteroid, Cytokines, Growth Factors and Hormones, Hormones, Steroid Hormones, T
  • {SNA} Androgen, Bioactive Small Molecule Alphabetical Index, Corticosteroid, Cytokines, Growth Factors and Hormones, Hormones, Steroid Hormones, T, 生物活性小分子, 细胞信号转导和神经科学, 细胞生物学

产品应用

  • Trilostane is an inhibitor of 3β-hydroxysteroid dehydrogenase used in the treatment of Cushing's syndrome. It was withdrawn from the United States market in April 1994. However, it was recently approved in 2008 for the treatment of Cushing's disease (hyperandrenocorticism) in dogs. It is also the first drug approved to treat both pituitary- and adrenal-dependent Cushing's in dogs. This prescription drug works by stopping the production of cortisol in the adrenal glands.

相关文献及参考

  • Komanicky, P., et al.: J. Clin. Endocrinol. Metab., 47, 1042 (1978),
  • Mori, Y., et al., Chem. Pharm. Bull., 29, 2646 (1981),
  • Thomas JL, et al., Selective inhibition of human 3β-hydroxysteroid dehydrogenase type 1 as a potential treatment for breast cancer. J. Steroid Biochem. Mol. Biol. 125 , 57-65, (2011) 摘要
  • Mori D, et al., Anti-ovulatory effects of RU486 and trilostane involve impaired cyclooxygenase-2 expression and mitotic activity of follicular granulosa cells in rats. Prostaglandins Other Lipid Mediat. 94 , 118-123, (2011) 摘要
  • Evaul K, et al., 3beta-hydroxysteroid dehydrogenase is a possible pharmacological target in the treatment of castration-resistant prostate cancer. Endocrinology 151 , 3514-3520, (2010) 摘要

安全信息

GHS Symbol
Precautionary statements
Signal word
Hazard statements
  • H361 Suspected of damaging fertility or the unborn child 怀疑对生育能力或未出生婴儿造成伤害
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
WGK Germany3
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R62 Possible risk of impaired fertility 有削弱生殖能力的危险
RTECSBV8044200 
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kil

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 109 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   IYKEDH Iyakuhin Kenkyu.  Study of Medical Supplies.  (Nippon Koteisho
   Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan)  V.1- 1970- 
   Volume(issue)/page/year: 17,365,1986

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >15 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NIIRDN Drugs in Japan (Ethical Drugs).  (Yakugyo Jiho Co., Ltd., Tokyo,
   Japan)  Volume(issue)/page/year: -,752,1990

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 7050 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   IYKEDH Iyakuhin Kenkyu.  Study of Medical Supplies.  (Nippon Koteisho
   Kyokai, 12-15, 2-chome, Shibuya, Shibu

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1055 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   YKYUA6 Yakkyoku.  Pharmacy.  (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo,
   Japan)  V.1-    1950-  Volume(issue)/page/year: 37,1637,1986

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Primate - monkey
DOSE                    : 5 mg/kg
SEX/DURATION            : female 25-29 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - abortion
REFERENCE :
   FESTAS Fertility and Sterility.  (American Fertility Soc., 608 13th Ave. S,
   Birmingham, AL 35282) V.1-    1950-  Volume(issue)/page/year: 32,464,1979

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 1050 mg/kg
SEX/DURATION            : male 7 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - other effects on male
REFERENCE :
   ARZNAD Arzneimittel-Forschung. Drug Research.  (Editio Cantor Verlag,
   Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.)  V.1-    1951-
   Volume(issue)/page/year: 33,754,1983

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - man
DOSE                    : 48 mg/kg
SEX/DURATION            : male 14 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - other effects on male
REFERENCE :
   ARZNAD Arzneimittel-Forschung. Drug Research.  (Editio Cantor Verlag,
   Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.)  V.1-    1951-
   Volume(issue)/page/year: 33,754,1983

Hazard Codes Xi
Storage condition Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

系列性分类

  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Cytokines, Growth Factors and Hormones - Cell Signaling and Neuroscience
  5. Hormones - Cytokines, Growth Factors and Hormones
  6. Steroid Hormones - Hormones
  7. Androgen - Steroid Hormones
  1. Medical Research Areas
  2. Metabolism
  3. Dehydrogenase

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