1797. Carbidopa

Nomenclature

CAS number: 28860-95-9
(αS)-α-Hydrazino-3,4-dihydroxy-α-methylbenzenepropanoic acid monohydrate; (-)-l-α-hydrazino-3,4-dihydroxy-α-methylhydrocinnamic acid monohydrate; α-hydrazino-α-methyl-β-(3,4-dihydroxyphenyl)propionic acid monohydrate; l-α-(3,4-dihydroxybenzyl)-α-hydrazinopropionic acid monohydrate; α-methyldopahydrazine; HMD; MK-486; Lodosyn (Merck & Co.).
C10H14N2O4.H2O; mol wt 244.24.
C 49.18%, H 6.60%, N 11.47%, O 32.75%.

Description and references

Peripheral decarboxylase inhibitor. Prepn of dl-form: Pfister, FR M1553 (1962 to Merck & Co.), C.A. 59, 12921e (1963); Sletzinger et al., J. Med. Chem. 6, 101 (1963); GB 940596; Chemerda et al., US 3462536 (1963, 1969 both to Merck & Co.). Synthesis of the l-form: Karady et al., DE 2062285; DE 2062332 (both 1971 to Merck & Co.), C.A. 75, 118122t, 118120r (1971); eidem, J. Org. Chem. 36, 1946, 1949 (1971). Inhibition of dopa decarboxylase: Porter et al., Biochem. Pharmacol. 11, 1067 (1962); Moran, Sourkes, J. Pharmacol. Exp. Ther. 148, 252 (1962); Watanabe et al., Clin. Pharmacol. Ther. 11, 740 (1970). Only the l-form is pharmacologically active: Lotti, Porter, J. Pharmacol. Exp. Ther. 172, 406 (1970).

Chemical structure

Properties

Crystals from hot water, mp 203-205° (dec). [α]D -17.3° (methanol). Also reported as mp 208°.

Derivative

Combination with levodopa.

Nomenclature

CAS number: 57308-51-7
Co-careldopa; Isicom (Desitin); Nacom (Merck & Co.); Sinemet (Merck & Co.).

Derivative

dl-Form.

Properties

Tan fluffy crystals, mp 206-208° (dec). uv max (methanol): 282.5 nm (ε 2940).

Therapeutic Category

In combination with levodopa as antiparkinsonian.

Keywords

Antiparkinsonian