Centchroman
Title: Centchroman
CAS Registry Number: 31477-60-8
CAS Name: rel-1-[2-[4-[(3R,4R)-3,4-Dihydro-7-methoxy-2,2-dimethyl-3-phenyl-2H-1-benzopyran-4-yl]phenoxy]ethyl]pyrrolidine
Additional Names: (trans)-1-[2-[p-(7-methoxy-2,2-dimethyl-3-phenyl-4-chromanyl)phenoxy]ethyl]pyrrolidine; 3,4-trans-2,2-dimethyl-3-phenyl-4-[p-(b-pyrrolidinoethoxy)phenyl]-7-methoxychroman; trans-centchroman; ormeloxifene
Trademarks: Centron (Torrent); Saheli (Hindustan Latex)
Molecular Formula: C30H35NO3
Molecular Weight: 457.60
Percent Composition: C 78.74%, H 7.71%, N 3.06%, O 10.49%
Literature References: Estrogen antagonist; synthetic nonsteroidal postcoital antifertility agent. Pharmacology: V. P. Kamboj et al., Indian J. Exp. Biol. 9, 103 (1971); idem et al., ibid. 15, 1144 (1977). Prepd (not claimed): J. W. Bolger, DE 2329201 (1974 to Riker); idem, US 3822287 (1974 to Rexall); S. Ray et al., J. Med. Chem. 19, 276 (1976). Mechanism of action: M. S. Sankaran, M. R. N. Prasad, Contraception 9, 279 (1974). Clinical pharmacology: R. Vaidya et al., ibid. 1173. Physicochemical properties: R. K. Seth et al., Indian J. Pharm. Sci. 45, 14 (1983). Resolution and stereoselective binding of enantiomers: M. Salman et al., J. Med. Chem. 29, 1801 (1986). Absolute configuration: N. Srivastava et al., Bioorg. Med. Chem. Lett. 6, 1747 (1996). HPLC determn in serum and milk: J. Lal et al., J. Chromatogr. B 658, 193 (1994). Clinical pharmacokinetics: idem et al., Contraception 52, 297 (1995). Toxicity: I. M. Chak et al., Indian J. Exp. Biol. 15, 1159 (1977). Review of clinical experience: M. M. Singh, Med. Res. Rev. 21, 302-347 (2001).
Properties: Crystals from ether/petr ether, mp 99-101°, sinters ~50°.
Melting point: mp 99-101°
 
Derivative Type: Hydrochloride
CAS Registry Number: 51023-56-4
Manufacturers' Codes: 6720 CDRI
Molecular Formula: C30H35NO3.HCl
Molecular Weight: 494.06
Percent Composition: C 72.93%, H 7.34%, N 2.84%, O 9.72%, Cl 7.18%
Properties: White crystals, mp 165-166°. uv max (methanol): 232, 278 nm (e 3701 at 278 nm). pKa 2.1. Sol in 10 parts chloroform, 20 parts acetone, 60 parts 95% ethanol, 20 parts methanol. Practically insol in water, isobutanol, 0.1N HCl, 0.1N NaOH. LD50 i.p. in mice: 400 mg/kg (Chak).
Melting point: mp 165-166°
pKa: pKa 2.1
Absorption maximum: uv max (methanol): 232, 278 nm (e 3701 at 278 nm)
Toxicity data: LD50 i.p. in mice: 400 mg/kg (Chak)
 
Derivative Type: (-)-Form
CAS Registry Number: 78994-23-7
Additional Names: Levormeloxifene
Properties: Prepd as hydrochloride, mp 197°. [a] D20 -192.9° (c = 1.0 in CHCl3).
Melting point: mp 197°
Optical Rotation: [a] D20 -192.9° (c = 1.0 in CHCl3)
 
Therap-Cat: Oral contraceptive.
Keywords: Contraceptive (Oral).

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