(1S,2R,10R,11S,14R,15S)-15-methyl-14-(prop-2-en-1-yl)tetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-ol

• ChemBase ID: 1239
• Molecular Formular: C21H32O
• Molecular Mass: 300.47818
• Monoisotopic Mass: 300.24531564
• SMILES: O[C@@]1([C@@]2([C@H]([C@H]3[C@H](CC2)[C@@H]2C(=CCCC2)CC3)CC1)C)CC=C
• Canonical SMILES: C=CC[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CCCC[C@H]12
• InChI: InChI=1S/C21H32O/c1-3-12-21(22)14-11-19-18-9-8-15-6-4-5-7-16(15)17(18)10-13-20(19,21)2/h3,6,16-19,22H,1,4-5,7-14H2,2H3/t16-,17+,18+,19-,20-,21-/m0/s1
• InChIKey: ATXHVCQZZJYMCF-XUDSTZEESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-15-methyl-14-(prop-2-en-1-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-ol; (1S,2R,10R,11S,14R,15S)-15-methyl-14-(prop-2-en-1-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-ol
• IUPAC Traditional name: gestanin; allylestrenol
• Brand Name: Perselin; Turinal; Gestanol; Gestanon; Gestormone; Orageston; Organon; Gestanin
• Synonyms: 17α-Allylestr-4-en-17β-ol; Allylestrenol

Database IDs

• CAS Number: 432-60-0
• PubChem SID: 46506946; 160964699
• PubChem CID: 235905
• ATC CODE: G03DC01
• CHEMBL: 1445549
• Chemspider ID: 205855
• DrugBank ID: DB01431
• KEGG ID: D01374
• Unique Ingredient Identifier: I47VB5DZ8O
• Wikipedia Title: Allylestrenol

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 4.828528
• LogD (pH = 7.4): 4.8285284
• Log P: 4.8285284
• Molar Refractivity: 93.1439 cm^3
• Polarizability: 36.66564 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 5.14
• LOG S: -5.73
• Solubility (Water): 5.58e-04 g/l

PROPERTIES

Pharmacology Properties

• Pregnancy Category: Used in threatened miscarriage and RPL

DETAILS

DrugBank - DB01431

• Drug Groups: approved
• Description: A synthetic steroid with progestational activity. [PubChem]
• Indication: Allylestrenol was designed to be used for miscarriage prevention, prevention of premature labour and has been investigated for possible use in men for treatment for benign prostatic hyperplasia.
• Pharmacology: Allylestrenol is a progestogen structurally related to progesterone that has been given in threatened and recurrent miscarriage, and to prevent premature labour. However, with the exception of proven progesterone deficiency, such use is no longer recommended. In threatened miscarriage in progesterone-deficient women a suggested dose is 5 mg three times daily by mouth for 5 to 7 days.
• Elimination: The glucuronide and sulfate conjugates of pregnanediol and pregnanolone are excreted in the urine and bile. Progesterone metabolites which are excreted in the bile may undergo enterohepatic recycling or may be excreted in the feces. Progesterone metabolites are excreted mainly by the kidneys.