cycloserine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 80 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2B,CAMK2D,CDK5,EIF2AK3,GRK2,ITK,MAPK7,NTRK2,PDK2,PRKDC,TEK 11
kinase-selectivity-class AKT1,CAMK2B,CAMK2D,CHUK,CLK2,CLK4,IRAK1,IRAK4,MAP3K14,MAP3K7,PDK1,SIK2,STK33 13
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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 265.96 33.95 89 2057 72367 90553934
Drug resistance 180.46 33.95 54 2092 30395 90595906
Neuropathy peripheral 174.61 33.95 78 2068 136892 90489409
Drug reaction with eosinophilia and systemic symptoms 131.04 33.95 46 2100 42712 90583589
Anaemia 90.22 33.95 71 2075 352731 90273570
Off label use 56.30 33.95 96 2050 1102156 89524145
Optic neuropathy 56.21 33.95 13 2133 2685 90623616
Optic neuritis 52.22 33.95 16 2130 9662 90616639
Hepatotoxicity 51.51 33.95 24 2122 45818 90580483
Tuberculoma of central nervous system 46.52 33.95 8 2138 364 90625937
Psychotic disorder 37.10 33.95 17 2129 31213 90595088

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 384.94 31.83 137 2690 47808 42570700
Neuropathy peripheral 175.07 31.83 99 2728 101754 42516754
Hepatotoxicity 153.60 31.83 59 2768 25108 42593400
Off label use 84.19 31.83 150 2677 638185 41980323
Toxic optic neuropathy 76.74 31.83 17 2810 1023 42617485
Optic neuritis 74.78 31.83 22 2805 4120 42614388
Drug resistance 71.55 31.83 38 2789 34210 42584298
Anaemia 68.27 31.83 88 2739 280190 42338318
Intentional product use issue 58.85 31.83 44 2783 71789 42546719
Optic neuropathy 52.71 31.83 15 2812 2497 42616011
Drug-induced liver injury 46.76 31.83 30 2797 38243 42580265
Arrhythmia 33.64 31.83 25 2802 40292 42578216
Benign soft tissue neoplasm 33.47 31.83 6 2821 120 42618388

FDA Adverse Event Reporting System (Geriatric)

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 611.83 31.98 217 4831 108743 110475508
Neuropathy peripheral 368.85 31.98 174 4874 179103 110405148
Hepatotoxicity 199.10 31.98 83 4965 63317 110520934
Drug resistance 198.12 31.98 80 4968 56294 110527957
Anaemia 152.80 31.98 154 4894 546932 110037319
Off label use 133.75 31.98 241 4807 1499944 109084307
Optic neuritis 126.55 31.98 38 5010 11109 110573142
Drug reaction with eosinophilia and systemic symptoms 118.89 31.98 63 4985 82032 110502219
Optic neuropathy 108.94 31.98 28 5020 4630 110579621
Toxic optic neuropathy 90.30 31.98 19 5029 1309 110582942
Intentional product use issue 71.06 31.98 71 4977 247835 110336416
Psychotic disorder 56.96 31.98 33 5015 50904 110533347
Drug-induced liver injury 55.38 31.98 45 5003 120022 110464229
Tuberculoma of central nervous system 54.68 31.98 11 5037 606 110583645
Tuberculosis 48.18 31.98 21 5027 17753 110566498
Vomiting 46.21 31.98 117 4931 910558 109673693
Aspartate aminotransferase increased 46.12 31.98 46 5002 159890 110424361
Pathogen resistance 41.87 31.98 19 5029 17653 110566598
Arrhythmia 38.38 31.98 29 5019 69546 110514705
Pulmonary tuberculosis 35.62 31.98 14 5034 9125 110575126
Benign soft tissue neoplasm 35.21 31.98 6 5042 131 110584120
Tinnitus 35.10 31.98 26 5022 60514 110523737
Peripheral sensory neuropathy 33.51 31.98 16 5032 16664 110567587
Hypokalaemia 32.79 31.98 41 5007 182407 110401844

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J04AB01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOBACTERIALS
DRUGS FOR TREATMENT OF TUBERCULOSIS
Antibiotics
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000892 Anti-Infective Agents, Urinary
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000904 Antibiotics, Antitubercular
MeSH PA D000963 Antimetabolites
MeSH PA D000995 Antitubercular Agents
CHEBI has role CHEBI:33231 antitubercular agent
CHEBI has role CHEBI:33282 antibacterial agent
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:35474 anxiolytic drug
CHEBI has role CHEBI:35476 antipsychotic agent
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:63726 neuroprotective agent

Related Drugs by ATC class:

J04AB Antibiotics 6 drugs
capreomycinenviomycinrifabutinrifampicinrifamycinrifapentine

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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
204225 RXNORM
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
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 mg ORAL ANDA 12 sections
Seromycin HUMAN PRESCRIPTION DRUG LABEL 1 13845-1203 CAPSULE 250 mg ORAL ANDA 21 sections
Cycloserine HUMAN PRESCRIPTION DRUG LABEL 1 43598-235 CAPSULE 250 mg ORAL ANDA 13 sections