14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-5-yl N,N-bis(2-chloroethyl)carbamate

• ChemBase ID: 1066
• Molecular Formular: C23H31Cl2NO3
• Molecular Mass: 440.40314
• Monoisotopic Mass: 439.16809922
• SMILES: ClCCN(C(=O)Oc1cc2c(C3C(C4C(C(O)CC4)(CC3)C)CC2)cc1)CCCl
• Canonical SMILES: ClCCN(C(=O)Oc1ccc2c(c1)CCC1C2CCC2(C1CCC2O)C)CCCl
• InChI: InChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3
• InChIKey: FRPJXPJMRWBBIH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-5-yl N,N-bis(2-chloroethyl)carbamate
• IUPAC Traditional name: estramustine
• Brand Name: Emcyt; Estracyt
• Synonyms: Estramustinum [INN-Latin]; Estramustine Sodium Phosphate; Estramustina [INN-Spanish]; Estramustin Sodium Phosphate; Estramustine

Database IDs

• CAS Number: 2998-57-4
• PubChem SID: 160964529
• PubChem CID: 18140

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.377693
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.099114
• LogD (pH = 7.4): 5.099114
• Log P: 5.099114
• Molar Refractivity: 116.2129 cm^3
• Polarizability: 45.46336 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.97
• LOG S: -6.06
• Solubility (Water): 3.85e-04 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 5.7

DETAILS

DrugBank - DB01196

• Drug Groups: approved
• Description: A nitrogen mustard linked to estradiol, usually as phosphate; used to treat prostatic neoplasms; also has radiation protective properties. [PubChem]
• Indication: For the palliative treatment of patients with metastatic and/or progressive carcinoma of the prostate
• Pharmacology: Estramustine is an antineoplastic agent indicated in the palliative treatment of patients with metastatic and/or progressive carcinoma of the prostate. Estramustine is a combination of estradiol with nitrogen mustard. In vivo, the nitrogen-mustard moiety becomes active and participates in alkylation of DNA or other cellular components.. This causes DNA damage in rapidly dividing cancerous cells leading to cell death and ideally, tumor shrinkage.
• Affected Organisms: Humans and other mammals
• Half Life: 20 hours
• Elimination: The metabolic urinary patterns of the estradiol moiety of estramustine phosphate and estradiol itself are very similar, although the metabolites derived from estramustine phosphate are excreted at a slower rate.
• External Links: Wikipedia; RxList; Drugs.com