cycloserine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
759 68-41-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cycloserine
  • seromycin
  • oxamycin
  • farmiserina
  • miroseryn
  • cyclorin
  • (R)-4-amino-1,2-oxazolidin-3-one
Antibiotic substance produced by Streptomyces garyphalus.
  • Molecular weight: 102.09
  • Formula: C3H6N2O2
  • CLOGP: -1.19
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 64.35
  • ALOGS: 0.93
  • ROTB: 0

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.75 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 100 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 65 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 163.58 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 80 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
June 29, 1964 FDA PURDUE GMP

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Electrocardiogram QT prolonged 168.41 32.00 63 1521 56340 53291142
Drug resistance 121.14 32.00 38 1546 19924 53327558
Tuberculosis 88.18 32.00 26 1558 11045 53336437
Neuropathy peripheral 85.01 32.00 47 1537 103140 53244342
Drug reaction with eosinophilia and systemic symptoms 77.54 32.00 31 1553 32769 53314713
Psychotic disorder 53.98 32.00 22 1562 24363 53323119
Optic neuropathy 47.39 32.00 11 1573 1839 53345643
Tuberculoma of central nervous system 45.13 32.00 8 1576 345 53347137
Intentional product use issue 38.63 32.00 25 1559 72469 53275013
Pulmonary tuberculosis 36.81 32.00 11 1573 4870 53342612
Anaemia 36.77 32.00 43 1541 276675 53070807
Off label use 36.14 32.00 56 1528 472156 52875326
Hepatotoxicity 35.29 32.00 17 1567 27863 53319619

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Electrocardiogram QT prolonged 226.44 31.89 86 1872 39555 32472013
Tuberculosis 165.26 31.89 47 1911 8682 32502886
Neuropathy peripheral 99.06 31.89 60 1898 76922 32434646
Hepatotoxicity 82.16 31.89 34 1924 19303 32492265
Intentional product use issue 70.38 31.89 39 1919 42172 32469396
Off label use 66.03 31.89 86 1872 306234 32205334
Drug resistance 54.79 31.89 27 1931 22938 32488630
Optic neuritis 49.66 31.89 15 1943 3387 32508181
Optic neuropathy 44.98 31.89 12 1946 1735 32509833
Vomiting 32.78 31.89 54 1904 235503 32276065

Pharmacologic Action:

SourceCodeDescription
ATC J04AB01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOBACTERIALS
DRUGS FOR TREATMENT OF TUBERCULOSIS
Antibiotics
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000892 Anti-Infective Agents, Urinary
MeSH PA D000904 Antibiotics, Antitubercular
MeSH PA D000963 Antimetabolites
MeSH PA D000995 Antitubercular Agents
MeSH PA D009676 Noxae
CHEBI has role CHEBI:25212 metabolites
CHEBI has role CHEBI:33231 antitubercular
CHEBI has role CHEBI:35221 antimetabolite
CHEBI has role CHEBI:35441 anti-infective drugs
CHEBI has role CHEBI:64571 NMDAR agonist

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Acute tuberculosis indication 25629007
Pulmonary tuberculosis indication 154283005 DOID:2957
Escherichia coli urinary tract infection indication 301011002
Bacterial urinary infection indication 312124009
Tuberculosis of meninges off-label use 58437007
Mycobacteriosis off-label use 88415009
Alcoholism contraindication 7200002
Depressive disorder contraindication 35489007
Sideroblastic anemia contraindication 41841004 DOID:8955
Megaloblastic anemia contraindication 53165003 DOID:13382
Acute nephropathy contraindication 58574008
Psychotic disorder contraindication 69322001
Severe anxiety (panic) contraindication 80583007
Epilepsy contraindication 84757009 DOID:1826
Kidney disease contraindication 90708001 DOID:557
Folic acid deficiency contraindication 190633005
Cobalamin deficiency contraindication 190634004
CNS Toxicity contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.38 acidic
pKa2 6.74 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Glutamate receptor ionotropic, NMDA 3A Ion channel IC50 5.64 WOMBAT-PK
Glutamate receptor ionotropic, NMDA 2B Ion channel IC50 5.64 WOMBAT-PK
Glutamate receptor ionotropic, NMDA 2C Ion channel IC50 5.34 WOMBAT-PK
Glutamate receptor ionotropic, NMDA 2D Ion channel IC50 5.64 WOMBAT-PK
Glutamate receptor ionotropic, NMDA 1 Ion channel IC50 5.26 WOMBAT-PK
Glutamate receptor ionotropic, NMDA 3B Ion channel IC50 5.64 WOMBAT-PK
Glutamate receptor ionotropic, NMDA 2A Ion channel IC50 5.64 WOMBAT-PK
Cytochrome P450 3A4 Enzyme IC50 4.31 WOMBAT-PK
Alanine racemase Enzyme INHIBITOR CHEMBL CHEMBL
D-alanine--D-alanine ligase Enzyme INHIBITOR CHEMBL CHEMBL
Alanine racemase Enzyme WOMBAT-PK
Glutamate receptor ionotropic, NMDA 1 Ion channel IC50 5.13 CHEMBL
Glutamate receptor ionotropic, NMDA 2C Ion channel EC50 4.74 CHEMBL
Glutamate NMDA receptor Ion channel IC50 5.64 CHEMBL

External reference:

IDSource
95IK5KI84Z UNII
4019284 VUID
N0000147483 NUI
D00877 KEGG_DRUG
C0010590 UMLSCUI
CHEBI:23503 CHEBI
4AX PDB_CHEM_ID
CHEMBL771 ChEMBL_ID
6234 PUBCHEM_CID
DB00260 DRUGBANK_ID
D003523 MESH_DESCRIPTOR_UI
577 INN_ID
204225 RXNORM
1617 MMSL
4520 MMSL
51619 MMSL
d01101 MMSL
002788 NDDF
387282000 SNOMEDCT_US
51334008 SNOMEDCT_US
4019284 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
SEROMYCIN HUMAN PRESCRIPTION DRUG LABEL 1 13845-1200 CAPSULE 250 mg ORAL ANDA 19 sections
CYCLOSERINE HUMAN PRESCRIPTION DRUG LABEL 1 13845-1201 CAPSULE 250 mg ORAL ANDA 19 sections
Cycloserine HUMAN PRESCRIPTION DRUG LABEL 1 13845-1202 CAPSULE 250 1 ORAL ANDA 2 sections
Seromycin HUMAN PRESCRIPTION DRUG LABEL 1 13845-1203 CAPSULE 250 mg ORAL ANDA 21 sections