Details of the Drug

General Information of Drug (ID: DMEPWYA)

Drug Name
THIOCOLCHICOSIDE
Synonyms
Thiocolchicoside; 602-41-5; Coltramyl; UNII-T1X8S697GT; Thiocolchicine 2-glucoside analog; NSC 147755; Musco-ril; T1X8S697GT; 10-Thiocolchicoside; Tiocolchicoside [DCIT]; Colchicoside, 10-thio-; Thiocolchicoside [INN:DCF]; Q-201823; Thiocolchicosidum [INN-Latin]; Tiocolchicosido [INN-Spanish]; C27H33NO10S; Tiocolchicosido; Tiocolchicoside; Muscoril; Thiocolchicosidum; EINECS 210-017-7; BRN 0072205; R. 271; 2-10-Di(demethoxy)-2-glucosyloxy-10-methylthiocolchicine; Miotens; Coltrax; NSC147755; Coltramyl (TN); NCGC00016519-01
Indication
Disease Entry ICD 11 Status REF
Muscle spasm MB47.3 Approved [1]
Affected Organisms
Humans and other mammals
ATC Code
M03BX05: THIOCOLCHICOSIDE
M03BX: Other centrally acting agents
M03B: MUSCLE RELAXANTS, CENTRALLY ACTING AGENTS
M03: MUSCLE RELAXANTS
M: MUSCULO-SKELETAL SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 563.6
Logarithm of the Partition Coefficient (xlogp) -0.4
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 11
ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 283 mcgh/L [2]
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 113 mcg/L [2]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 30 min [2]
Elimination
Thiocolchicoside is not eliminated unchanged, rather as one of three metabolites found in either feces (~79 %) or in urine 20% [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 7.7 hours [3]
Metabolism
The drug is metabolized via the either conjugation [4]
Vd
The volume of distribution (Vd) of drug is 42.7 L [2]
Chemical Identifiers
Formula
C27H33NO10S
IUPAC Name
N-[(7S)-1,2-dimethoxy-10-methylsulfanyl-9-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
Canonical SMILES
CC(=O)N[C@H]1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)SC)OC)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
InChI
InChI=1S/C27H33NO10S/c1-12(30)28-16-7-5-13-9-18(37-27-24(34)23(33)22(32)19(11-29)38-27)25(35-2)26(36-3)21(13)14-6-8-20(39-4)17(31)10-15(14)16/h6,8-10,16,19,22-24,27,29,32-34H,5,7,11H2,1-4H3,(H,28,30)/t16-,19+,22+,23-,24+,27+/m0/s1
InChIKey
LEQAKWQJCITZNK-AXHKHJLKSA-N
Cross-matching ID
PubChem CID
9915886
ChEBI ID
CHEMBL213907
CAS Number
602-41-5
UNII
T1X8S697GT
DrugBank ID
DB11582
TTD ID
D0IG4I
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
GABA(A) receptor alpha-1 (GABRA1) TT1MPAY GBRA1_HUMAN Inhibitor [5]
GABA(A) receptor beta-2 (GABRB2) TTZA1NY GBRB2_HUMAN Inhibitor [5]
GABA(A) receptor gamma-2 (GABRG2) TT06RH5 GBRG2_HUMAN Inhibitor [5]
Gamma-aminobutyric acid receptor (GAR) TTNJYV2 NOUNIPROTAC Inhibitor [5]
Glycine receptor (GlyR) TTZ8EM9 GLRA1_HUMAN ; GLRA2_HUMAN ; GLRA3_HUMAN ; GLRA4_HUMAN ; GLRB_HUMAN Inhibitor [5]
Strychnine-binding glycine receptor (GLRA1) TTF45NW GLRA1_HUMAN Inhibitor [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Thiocolchicine EMA label
3 Review of the toxicology, pharmacodynamics and pharmacokinetics of thiocolchicoside, a GABA-agonist muscle relaxant with anti-inflammatory and analgesic actions
4 THIOCOLCHICOSIDE AS MUSCLE RELAXANT: A REVIEW
5 3-demethoxy-3-glycosylaminothiocolchicines: Synthesis of a new class of putative muscle relaxant compounds. J Med Chem. 2006 Sep 7;49(18):5571-7.