Bucillamine

HCID 656604CAS 65002-17-7

Substructure search Find similar structures

Basic information

Standard SMILES: CC(C)(S)C(=O)N[C@@H](CS)C(=O)O
InChIKey: VUAFHZCUKUDDBC-BYPYZUCNSA-N
Molecular formula: C7H13NO3S2
Average molar mass: 223.3 g/mol
Monoisotopic mass: 223.03368528

Overview

Bucillamine is an organic molecular entity.

Names & identifiers

Preferred name: Bucillamine
IUPAC: (2R)-2-[(2-methyl-2-sulfanylpropanoyl)amino]-3-sulfanylpropanoic acid
English name: Bucillamine
Molecular formula: C7H13NO3S2
Molecular weight: 223.31

Names & synonyms

bucillamine65002-17-7TiobutaritBucilantBucilaminaN-(2-Mercapto-2-methylpropionyl)-L-cysteineBucillaminumDTXSID2048587R80LRA5WTFSA-96DE019L-CYSTEINE, N-(2-MERCAPTO-2-METHYL-1-OXOPROPYL)-

Show more names

sa96de-019Bucillamine 95%BUCILLAMINE USP/EP/BPBucillamine, 10 mM in DMSON-(2-Mercaptoisobutyryl)cysteine

(2R)-2-(2-METHYL-2-SULFANYLPROPANAMIDO)-3-SULFANYLPROPANOIC ACIDDTXCID2028513RefChem:917687M01CC02(2R)-2-(2-Methyl-2-sulfanylpropanoylamino)-3-sulfanylpropanoic acid2-mercapto-2-methylpropanoyl-L-cysteineRimatilThiobutarit

Database identifiers

CAS: 65002-17-7
PubChem CID: 656604
DTXSID: DTXSID2048587
ChEMBL: CHEMBL80830
ChEBI: CHEBI:31312
UNII: R80LRA5WTF
Nikkaji: J22.800A

Properties

Computed structural properties

XLogP: 0.4
Topological polar surface area: 68.4 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 5
Rotatable bonds: 4
Heavy atoms: 13
Formal charge: 0
Complexity: 218

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Physicochemical properties

Melting point: 119 · 119-123°C
alpha: 25 · D25 +32.3° (c = 1.0 in ethanol)
Boiling point: 438 · 438.0±45.0 °C(Predicted)
Density: 1.3934 · 1.3934 (rough estimate)
refractive index: 1.637 · 1.6370 (estimate)
storage temp.: -20 °C · Hygroscopic, -20°C Freezer, Under Inert Atmosphere
solubility: DMSO (Very Slightly), Ethanol (Slightly), Methanol (Slightly), Water (Slightly)
pka: 3.01 · 3.01±0.10(Predicted)
form: Solid
color: White to Pale Yellow
Stability: Air Sensitive, Hygroscopic, Unstable in Solution
CAS DataBase Reference: 65002 · 65002-17-7(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 80 LRA5WTF · R80LRA5WTF
ATC code: 1 CC02 · M01CC02
Symbol(GHS): 5 · GHS05,GHS07,GHS09
Signal word: Danger
Hazard statements: 302 · H302-H318-H410
Precautionary statements: 273 · P273-P280-P301+P312+P330-P305+P351+P338+P310
Toxicity: 50 in · LD50 in mice (mg/kg): 2285 i.p.; 989.6 i.v. (Fujita, 1981)

Safety & regulation

Toxicology

Drug Induced Liver Injury · 4 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Bucillamine

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Safety data

Toxicity: LD50 in mice (mg/kg): 2285 i.p.; 989.6 i.v. (Fujita, 1981)
Signal word: Danger
Symbol(GHS): GHS05,GHS07,GHS09
Hazard statements: H302-H318-H410
Precautionary statements: P273-P280-P301+P312+P330-P305+P351+P338+P310

Chemistry & industry

Pharmacology

ATC Code · 2 items

M - Musculo-skeletal system

QM - Musculo-skeletal system

MeSH Pharmacological Classification · 2 items

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.

Applications · 2 items

DescriptionBucillamine is an orally active immunomodulator useful in the treatment of rheumatoid arthritis. Its potencies in inhibiting collagenase activity and inactivating rheumatoid factor far exceed those of penicillamine. In man, bucillamine reportedly brings about significant improvements over placebo in erythrocyte sedimentation, grip power, joint swelling and duration of morning stiffness.

UsesAn antirheumatic agent.