(17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl) N,N-bis(2-chloroethyl)carbamate
Basic information
- CAS
2998-57-4- Standard SMILES
CC12CCC3c4ccc(OC(=O)N(CCCl)CCCl)cc4CCC3C1CCC2O- InChIKey
FRPJXPJMRWBBIH-UHFFFAOYSA-N- Molecular formula
- C23H31Cl2NO3
- Average molar mass
- 440.4 g/mol
- Monoisotopic mass
- 439.1680992
Names & identifiers
- Preferred name
- (17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl) N,N-bis(2-chloroethyl)carbamate
- IUPAC
- (17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl) N,N-bis(2-chloroethyl)carbamate
- English name
- Estramustine
- Molecular formula
- C23H31Cl2NO3
- Molecular weight
- 440.4
Names & synonyms
(17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl) N,N-bis(2-chloroethyl)carbamateC23H31Cl2NO3NSC 89201MLS00270193617.beta.-Estradiol 3-(bis(2-chloroethyl)carbamate)CHEMBL290686SCHEMBL14031683SCHEMBL29349776FRPJXPJMRWBBIH-UHFFFAOYSA-NSMR001565519NS00004873Estradiol {3-[bis(2-chloroethyl)carbamate]}
Show more names
AlestramustineLEO 275EstractyNSC89201NSC-89201EstamustineEstramustinESTRAMUSTINEEstramustine USP/EP/BP
Estradiol, {3-[bis(2-chloroethyl)carbamate]}17.Beta.-Estradiol {3-[bis(2-chloroethyl)carbamate]}17-Hydroxyestra-1,3,5(10)-trien-3-yl bis(2-chloroethyl)carbamate17-Hydroxyestra-1,3,5(10)-trien-3-yl bis(2-chloroethyl)carbamate, (17.beta.)-Carbamic acid, bis(2-chloroethyl)-, 17.beta.-hydroxyestra-1,3,5(10)-trien-3-yl esterEstra-1,3,5(10)-triene-3, 17-diol, {3-[bis(2-chloroethyl)carbamate],} (17.beta.)-Estra-1,3,5(10)-triene-3,17-diol (17.beta.)-, {3-[bis(2-chloroethyl)carbamate]}Estra-1,3,5(10)-triene-3,17-diol (17.beta.)-, 3-[bis(2-chloroethyl)carbamate]
Properties
Computed structural properties
- XLogP
- 4
- Topological polar surface area
- 49.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 6
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 584
Experimental & physicochemical properties
DrugsPharmaceuticals
Physicochemical properties
- Melting point
- 104 · 104-105°
- alpha
- 20 · D20 +50° (in dioxane)
- Boiling point
- 565.8 · 565.8±50.0 °C(Predicted)
- Density
- 1.253 · 1.253±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- form
- Solid
- pka
- 15.05 · 15.05±0.40(Predicted)
- color
- White to off-white
- Water Solubility
- 1 mg/L · 1mg/L(30 ºC)
- InChIKey
- FRPJXPJMRWBBIH-SZZXFXARNA-N
- SMILES
- [C@@]12([H])CCC3C=C(OC(=O)N(CCCl)CCCl)C=CC=3[C@@]1([H])CC[C@]1(C)[C@H](CC[C@@]21[H])O |&1:0,20,24,26,29,r|
- CAS DataBase Reference
- 2998 · 2998-57-4(CAS DataBase Reference)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
UsesAntineoplastic.
UsesEstradiol 3-[N,N-Bis(2-chloroethyl)carbamate] is used treatment of breast cancer. Also used in the treatment of prostate cancer.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: A carbamate ester obtained by the formal condensation of the hydroxy group of 17beta-estradiol with the carboxy group of bis(2-chloroethyl)carbamic acid.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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