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

Stem definition	Drug id	CAS RN
	759	68-41-7

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
0.75	g	O

ADMET properties:

Property	Value	Reference
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

Approvals:

Date	Agency	Company	Orphan
June 29, 1964	FDA	PURDUE GMP

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Electrocardiogram QT prolonged	223.90	33.14	78	1732	59452	63427760
Drug resistance	125.64	33.14	40	1770	22893	63464319
Neuropathy peripheral	93.44	33.14	51	1759	113616	63373596
Drug reaction with eosinophilia and systemic symptoms	77.79	33.14	31	1779	33805	63453407
Anaemia	53.77	33.14	53	1757	293377	63193835
Psychotic disorder	53.69	33.14	22	1788	25690	63461522
Hepatotoxicity	52.17	33.14	24	1786	37017	63450195
Optic neuropathy	52.10	33.14	12	1798	2020	63485192
Tuberculoma of central nervous system	45.59	33.14	8	1802	339	63486873
Optic neuritis	43.19	33.14	14	1796	8421	63478791
Off label use	35.24	33.14	66	1744	674396	62812816

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Electrocardiogram QT prolonged	355.61	32.24	125	2269	40827	34913710
Hepatotoxicity	153.56	32.24	57	2337	21428	34933109
Neuropathy peripheral	112.11	32.24	70	2324	83193	34871344
Off label use	73.41	32.24	114	2280	419410	34535127
Intentional product use issue	64.89	32.24	44	2350	59772	34894765
Drug resistance	62.50	32.24	32	2362	25895	34928642
Optic neuritis	59.67	32.24	18	2376	3556	34950981
Anaemia	42.69	32.24	65	2329	233270	34721267
Optic neuropathy	42.05	32.24	12	2382	1953	34952584
Vomiting	35.76	32.24	62	2332	247559	34706978
Arrhythmia	35.61	32.24	25	2369	35783	34918754
Benign soft tissue neoplasm	33.48	32.24	6	2388	116	34954421

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Electrocardiogram QT prolonged	531.86	29.12	195	4142	90191	79649860
Neuropathy peripheral	213.41	29.12	118	4219	141187	79598864
Hepatotoxicity	195.26	29.12	81	4256	51271	79688780
Drug resistance	161.81	29.12	67	4270	42146	79697905
Off label use	101.67	29.12	178	4159	907037	78833014
Optic neuritis	100.60	29.12	32	4305	9488	79730563
Optic neuropathy	92.45	29.12	24	4313	3460	79736591
Intentional product use issue	90.36	29.12	71	4266	152041	79588010
Anaemia	86.25	29.12	113	4224	444902	79295149
Psychotic disorder	71.78	29.12	38	4299	41364	79698687
Drug reaction with eosinophilia and systemic symptoms	71.14	29.12	44	4293	64200	79675851
Tuberculoma of central nervous system	53.31	29.12	11	4326	576	79739475
Vomiting	52.50	29.12	113	4224	665715	79074336
Aspartate aminotransferase increased	44.90	29.12	46	4291	138595	79601456
Toxic optic neuropathy	40.79	29.12	10	4327	1143	79738908
Tuberculosis	38.32	29.12	18	4319	15180	79724871
Arrhythmia	37.15	29.12	29	4308	61243	79678808
Pathogen resistance	36.20	29.12	17	4320	14325	79725726
Product use in unapproved indication	35.60	29.12	55	4282	250304	79489747
Pulmonary tuberculosis	35.29	29.12	14	4323	7851	79732200
Peripheral sensory neuropathy	34.60	29.12	16	4321	13017	79727034
Benign soft tissue neoplasm	34.38	29.12	6	4331	126	79739925
Tinnitus	33.62	29.12	24	4313	44309	79695742
Hypothyroidism	32.20	29.12	25	4312	52367	79687684
Hypokalaemia	31.55	29.12	39	4298	144001	79596050
Polyneuropathy	30.46	29.12	18	4319	24133	79715918
Deafness	30.05	29.12	17	4320	21020	79719031
Gastrointestinal disorder	29.89	29.12	35	4302	122170	79617881

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
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 agents
CHEBI has role	CHEBI:35221	antimetabolite
CHEBI has role	CHEBI:35441	antiinfective agents
CHEBI has role	CHEBI:64571	NMDAR agonists

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
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 level	Dissociation constant	Type (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:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Glutamate receptor ionotropic, NMDA 3A	Ion channel	Q8TCU5	NMD3A_HUMAN		IC50	5.64	WOMBAT-PK
Glutamate receptor ionotropic, NMDA 2B	Ion channel	Q13224	NMDE2_HUMAN		IC50	5.64	WOMBAT-PK
Glutamate receptor ionotropic, NMDA 2C	Ion channel	Q14957	NMDE3_HUMAN		IC50	5.34	WOMBAT-PK
Glutamate receptor ionotropic, NMDA 2D	Ion channel	O15399	NMDE4_HUMAN		IC50	5.64	WOMBAT-PK
Glutamate receptor ionotropic, NMDA 1	Ion channel	Q05586	NMDZ1_HUMAN		IC50	5.26	WOMBAT-PK
Glutamate receptor ionotropic, NMDA 3B	Ion channel	O60391	NMD3B_HUMAN		IC50	5.64	WOMBAT-PK
Glutamate receptor ionotropic, NMDA 2A	Ion channel	Q12879	NMDE1_HUMAN		IC50	5.64	WOMBAT-PK
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN		IC50	4.31	WOMBAT-PK
Alanine racemase	Enzyme		ALR_MYCTU	INHIBITOR			CHEMBL	CHEMBL
D-alanine--D-alanine ligase	Enzyme		DDL_MYCTU	INHIBITOR			CHEMBL	CHEMBL
Alanine racemase	Enzyme		ALR_MYCTO				WOMBAT-PK
Glutamate receptor ionotropic, NMDA 1	Ion channel		NMDZ1_RAT		IC50	5.13	CHEMBL
Glutamate receptor ionotropic, NMDA 2C	Ion channel		NMDE3_RAT		EC50	4.74	CHEMBL
Glutamate NMDA receptor	Ion channel		NMDZ1_RAT NMDE1_RAT NMDE2_RAT NMDE3_RAT NMDE4_RAT NMD3B_RAT NMD3A_RAT		IC50	5.64	CHEMBL

External reference:

ID	Source
95IK5KI84Z	UNII
4019284	VUID
N0000147483	NUI
D00877	KEGG_DRUG
204225	RXNORM
4019284	VANDF
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

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
SEROMYCIN	HUMAN PRESCRIPTION DRUG LABEL	1	13845-1200	CAPSULE	250 mg	ORAL	ANDA	19 sections
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	13845-1201	CAPSULE	250 mg	ORAL	ANDA	19 sections
Cycloserine	HUMAN PRESCRIPTION DRUG LABEL	1	13845-1202	CAPSULE	250 mg	ORAL	ANDA	13 sections
Cycloserine	HUMAN PRESCRIPTION DRUG LABEL	1	13845-1202	CAPSULE	250 1	ORAL	ANDA	13 sections
Seromycin	HUMAN PRESCRIPTION DRUG LABEL	1	13845-1203	CAPSULE	250 mg	ORAL	ANDA	21 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