cycloserine indications/contra

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

Drug dosage:

DoseUnitRoute
0.75 g O

Approvals:

DateAgencyCompanyOrphan
June 29, 1964 FDA PURDUE GMP

FDA Adverse Event Reporting System

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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 130.94 43.22 30 282 10765 3374782
Neuropathy peripheral 107.87 43.22 28 284 16779 3368768
Tuberculosis 105.13 43.22 20 292 2873 3382674
Drug resistance 72.82 43.22 16 296 4647 3380900
Deafness 69.37 43.22 15 297 4039 3381508
Vomiting 68.45 43.22 30 282 89501 3296046
Hypothyroidism 63.79 43.22 15 297 5874 3379673
Psychotic disorder 62.83 43.22 16 296 8718 3376829
Confusional state 57.81 43.22 21 291 37977 3347570
Tinnitus 55.63 43.22 14 298 7251 3378296
Drug reaction with eosinophilia and systemic symptoms 54.48 43.22 14 298 7881 3377666
Ototoxicity 49.13 43.22 8 304 460 3385087
Tuberculoma of central nervous system 46.58 43.22 6 306 63 3385484
Gastrointestinal disorder 45.85 43.22 13 299 10556 3374991
Nausea 43.73 43.22 25 287 129620 3255927

Pharmacologic Action:

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SourceCodeDescription
ATC J04AB01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOBACTERIALS
DRUGS FOR TREATMENT OF TUBERCULOSIS
Antibiotics
CHEBI has role CHEBI:64571 NMDA receptor agonist
CHEBI has role CHEBI:35441 antiinfective agent
CHEBI has role CHEBI:33231 antitubercular agent
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
MeSH PA D012076 Renal Agents

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Acute tuberculosis indication 25629007
Pulmonary tuberculosis indication 154283005 DOID:2957
Escherichia coli urinary tract infection indication 301011002
Bacterial urinary infection indication 312124009
Alcoholism contraindication 7200002
Depressive disorder contraindication 35489007 DOID:2848
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:2527
Folic acid deficiency contraindication 190633005
Cobalamin deficiency contraindication 190634004
CNS Toxicity contraindication
Tuberculosis of meninges off-label use 58437007
Mycobacteriosis off-label use 88415009

Acid dissociation constants calculated using MoKa v3.0.0

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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:

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

External reference:

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IDSource
CHEBI:40009 CHEBI
DB00260 DRUGBANK_ID
4019284 VUID
N0000147483 NUI
C0010590 UMLSCUI
D00877 KEGG_DRUG
CHEMBL771 ChEMBL_ID
4019284 VANDF
N0000005955 NDFRT
N0000147483 NDFRT
3007 RXNORM
51619 MMSL
002788 NDDF
387282000 SNOMEDCT_US
51334008 SNOMEDCT_US
4520 MMSL
d01101 MMSL
95IK5KI84Z UNII
577 INN_ID
D003523 MESH_DESCRIPTOR_UI
6234 PUBCHEM_CID
4AX PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
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 1 sections