Cycloserine

Summary

Cycloserine (CHEMBL771) is an approved small-molecule antitubercular agent (ATC J04AB01); indicated across 34 conditions including tuberculosis and obsessive-compulsive disorder.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J04AB01
• Indications: 34 conditions
• Clinical trials: 113
• Chemistry: 102.09 Da · C3H6N2O2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL771
Name	Cycloserine
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	6234
ChEBI	CHEBI:40009
ATC	J04AB01
Molecular formula	C3H6N2O2
Molecular weight	102.09
InChIKey	DYDCUQKUCUHJBH-UWTATZPHSA-N

SMILES: C1[C@H](C(=O)NO1)N

IUPAC name: (4R)-4-amino-1,2-oxazolidin-3-one

ChEBI definition: A 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanine—D-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis).

Pharmacological roles (ChEBI): antitubercular agent, antiinfective agent, NMDA receptor agonist.

Other ChEBI roles (chemical / environmental): antimetabolite, metabolite.

Also known as: Cicloserina, Cycloserine, Cycloserinum, D-cycloserine, NSC-154851, NSC-76029, Orientomycin, Seromycin, D-Cycloserine, cycloserine, DL-Cycloserine, SID11110913

Parent form; salt/anhydrous children: CHEMBL1222336

Patent coverage: 7,201 distinct patent families (23,487 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 23 (assay-derived). Sample: Survival motor neuron protein, Prelamin-A/C, RecQ-like DNA helicase BLM, Glutamate NMDA receptor; GRIN1/GRIN2B, Glutamate NMDA receptor; GRIN1/GRIN2A, Glutamate NMDA receptor, Thyrotropin receptor, Menin/Histone-lysine N-methyltransferase MLL, Glutamate NMDA receptor; Grin1/Grin2b, Glutamate NMDA receptor; Grin1/Grin2a, Glutamate NMDA receptor; Grin1/Grin2c, Prostaglandin G/H synthase 1, Muscarinic acetylcholine receptor M1, Ionotropic glutamate receptor NMDA 1/2C, Ionotropic glutamate receptor NMDA 1/2D, Ionotropic glutamate receptor NMDA 1/2D, Glutamate receptor ionotropic, NMDA 1, Cytochrome P450 2C9, Cytochrome P450 3A4, Glutamate receptor ionotropic, NMDA 2C.

Bioactivity

ChEMBL activities: 25 potent at pChembl ≥ 5 of 50 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
BLM	8.96	Potency	1.1	nM	CHEMBL_ACT_4753886
BLM	8.96	Potency	1.1	nM	CHEMBL_ACT_4945753
GRIN2D	5.82	EC50	1500	nM	CHEMBL_ACT_29244593
HIF1A	5.8	Potency	1585	nM	CHEMBL_ACT_4117726
HIF1A	5.8	Potency	1585	nM	CHEMBL_ACT_4519777
P35439	5.64	IC50	2300	nM	CHEMBL_ACT_425582
P35439	5.55	EC50	2800	nM	CHEMBL_ACT_29223823
P35439	5.55	EC50	2800	nM	CHEMBL_ACT_29223827
P35439	5.54	EC50	2900	nM	CHEMBL_ACT_29244480
P35439	5.53	EC50	2950	nM	CHEMBL_ACT_422883
P35439	5.48	EC50	3300	nM	CHEMBL_ACT_29244478
TSHR	5.4	Potency	3981	nM	CHEMBL_ACT_3916029
TSHR	5.4	Potency	3981	nM	CHEMBL_ACT_3919999
TSHR	5.4	Potency	3981	nM	CHEMBL_ACT_4617572
TSHR	5.4	Potency	3981	nM	CHEMBL_ACT_4719179
GRIN1	5.35	EC50	4500	nM	CHEMBL_ACT_29244585
MAPK1	5.3	Potency	5012	nM	CHEMBL_ACT_4713768
LMNA	5.2	Potency	6310	nM	CHEMBL_ACT_3640387
GRIN1	5.13	EC50	7400	nM	CHEMBL_ACT_29244577
P35439	5.13	IC50	7370	nM	CHEMBL_ACT_422882
P35439	5.09	EC50	8200	nM	CHEMBL_ACT_29244476
P35439	5.08	EC50	8300	nM	CHEMBL_ACT_29223819
CYP3A4	5	Potency	10000	nM	CHEMBL_ACT_4949632
CYP3A4	5	Potency	10000	nM	CHEMBL_ACT_5018553
CYP3A4	5	AC50	10000	nM	CHEMBL_ACT_6045097

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

1 approved indication. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
tuberculosis	4	MONDO:0018076	MONDO:0000368

21 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
obsessive-compulsive disorder	3	MONDO:0008114	EFO:0004242
autism	3	MONDO:0005260	EFO:0003758
post-traumatic stress disorder	3	MONDO:0005146	EFO:0001358
panic disorder	3	MONDO:0005383	EFO:0004262
phobic disorder	3	MONDO:0003699	EFO:1001908
social phobia	3	MONDO:0001247	EFO:1001917
pulmonary tuberculosis	3	MONDO:0006052	EFO:1000049
cocaine dependence	2	MONDO:0005186	EFO:0002610
stroke disorder	2	MONDO:0005098	EFO:0000712
nicotine dependence	2	MONDO:0008575	EFO:0003768
drug dependence	2	MONDO:0005303	EFO:0003890
schizoaffective disorder	2	MONDO:0005487	EFO:0005411
opiate dependence	2	MONDO:0005530	EFO:0005611
agoraphobia	2	MONDO:0003709	EFO:1001872
major depressive disorder	2	MONDO:0002009	MONDO:0002009
brain injury	2	MONDO:0043510	MONDO:0043510
fibromyalgia	2	MONDO:0005546	EFO:0005687
bipolar disorder	2	MONDO:0004985	MONDO:0004985
pyelonephritis	2	MONDO:0006939	EFO:1001141
sleep apnea syndrome	1	MONDO:0005296	EFO:0003877
anxiety	1	MONDO:0011918	EFO:0005230

8 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 113.

Phase distribution

Phase	Trials
PHASE2	34
Not specified	25
PHASE4	15
PHASE3	13
EARLY_PHASE1	9
PHASE1	8
PHASE2/PHASE3	6
PHASE1/PHASE2	3

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00455702	PHASE4	COMPLETED	Effects of Weekly Dosing of D-cycloserine on Cognitive Function in Individuals With Schizophrenia
NCT00633984	PHASE4	COMPLETED	D-Cycloserine Enhancement of Exposure in Social Phobia
NCT00674570	PHASE4	COMPLETED	Veteran Stress and Learning Study
NCT00742079	PHASE4	COMPLETED	Using D-cycloserine to Enhance the Benefits of Cognitive Behavioral Therapy for Schizophrenia
NCT00964041	PHASE4	WITHDRAWN	Once Weekly D-cycloserine for Schizophrenia
NCT01490697	PHASE4	COMPLETED	Developing Memory Reconsolidation Blockers as Novel Posttraumatic Stress Disorder (PTSD) Treatments
NCT01649895	PHASE4	COMPLETED	D-Cycloserine as an Adjunct to Internet-CBT for OCD
NCT01833897	PHASE4	COMPLETED	NMDA Antagonists in Bipolar Depression
NCT01981759	PHASE4	COMPLETED	D-Cycloserine Augmentation of Cognitive Behavioral Therapy for Delusions
NCT02385266	PHASE4	TERMINATED	Treating Urological Chronic Pelvic Pain Syndrome (UCPPS) Pain
NCT02635893	PHASE4	COMPLETED	Lower Limb Function After Spinal Cord Injury
NCT02656342	PHASE4	COMPLETED	Translational Approach to the Understanding and Treatment of Obsessive-Compulsive Disorder (OCD). Can D-Cycloserine Enhance and Stabilize the Treatment-response in Relapsed and Non-responding OCD-patients?
NCT02772211	PHASE4	UNKNOWN	D-cycloserine for Relapse Prevention Following Intravenous Ketamine in Treatment-resistant Depression
NCT05306223	PHASE4	UNKNOWN	A Study of an Oral Short-course Regimen Including Bedaquiline for the Treatment of Participants With Multidrug-resistant Tuberculosis in China
NCT07542548	PHASE4	COMPLETED	D-Cycloserine for Serine Palmitoyltransferase Inhibition
NCT06081361	PHASE3	ACTIVE_NOT_RECRUITING	Innovating Shorter, All- Oral, Precised, Individualized Treatment Regimen for Rifampicin Resistant Tuberculosis：Contezolid, Delamanid and Bedaquiline Cohort
NCT07507214	PHASE2/PHASE3	NOT_YET_RECRUITING	Optimized, Neuroplasticity-Enhanced-Depression (ONE-D) Transcranial Magnetic Stimulation (TMS) Treatment for Female Athletes With Co-morbid Depression and Concussion
NCT00000371	PHASE3	COMPLETED	Trial of D-Cycloserine in Schizophrenia
NCT00000372	PHASE3	WITHDRAWN	Glycine and D-Cycloserine in Schizophrenia
NCT00182000	PHASE3	COMPLETED	Effectiveness of D-Cycloserine as an Aid to Enhance Learning for Individuals With OCD Receiving Behavior Therapy
NCT00198107	PHASE3	COMPLETED	Evaluating the Effectiveness of Aripiprazole and D-Cycloserine to Treat Symptoms Associated With Autism
NCT00198120	PHASE3	COMPLETED	Safety and Effectiveness of D-Cycloserine in Children With Autism
NCT00222235	PHASE2/PHASE3	COMPLETED	Adjunctive Treatment for Decreasing Symptoms of Schizophrenia
NCT00301080	PHASE3	TERMINATED	D-cycloserine in the Management of Chemotherapy-Induced Peripheral Neuropathic Pain
NCT00356278	PHASE2/PHASE3	COMPLETED	D-cycloserine and Virtual Reality Exposure to Treat Iraq War Veterans With PTSD
NCT00452231	PHASE2/PHASE3	UNKNOWN	RCT of CBT Combined With D-Cycloserine for Treating PTSD
NCT00515879	PHASE3	COMPLETED	Effect of D-cycloserine Plus Cognitive Behavioral Therapy on People With Social Phobia
NCT00926900	PHASE2/PHASE3	UNKNOWN	The Role of the Glutamatergic System in the Extinction of Conditioned Reinforcement Processes
NCT01086475	PHASE3	COMPLETED	D-Cycloserine and Social Skills Training in Autism Spectrum Disorders
NCT01102803	PHASE3	COMPLETED	D-Cycloserine to Enhance Cognitive Behavioral Therapy (CBT) for Acrophobia
NCT01399866	PHASE3	COMPLETED	Cognitive Remediation With D-Cycloserine
NCT01411774	PHASE3	COMPLETED	D-cycloserine Augmentation of Cognitive Behavioral Therapy (CBT) for Pediatric Obsessive-compulsive Disorder (OCD)
NCT01680107	PHASE3	TERMINATED	D-cycloserine Augmented CBT for Panic Disorder
NCT03216356	PHASE2/PHASE3	WITHDRAWN	Effect of D-cycloserine on a Short Imagery Rescripting Intervention for Subclinical PTSD
NCT05591677	PHASE2	ACTIVE_NOT_RECRUITING	D-Cycloserine Augmentation of Intermittent Theta Burst Stimulation (iTBS) in Depression (COGENT)
NCT06121284	PHASE2	RECRUITING	iTBS+D-Cycloserine for Youth Suicide
NCT07460947	PHASE1/PHASE2	NOT_YET_RECRUITING	A Pilot Trial of One-Day Accelerated TMS and D-cycloserine in Suicidal Patients With Borderline Personality Disorder
NCT07593222	PHASE1/PHASE2	NOT_YET_RECRUITING	Synaptic Mechanisms of Intermittent Theta Burst Stimulation for Major Depressive Disorder
NCT00000194	PHASE2	WITHDRAWN	Neurobiology of Opioid Dependence: 3 - 3
NCT00125528	PHASE2	COMPLETED	D-cycloserine in the Management of Chronic Low Back Pain
NCT00128401	PHASE2	COMPLETED	Use of an Antibiotic as an Enhancer for the Treatment of Social Phobia
NCT00257361	PHASE2	WITHDRAWN	D-Cycloserine Augmentation of Exposure and Response Prevention Treatment for Obsessive-Compulsive Disorder
NCT00408031	PHASE2	COMPLETED	D-cycloserine for Major Depressive Disorder
NCT00430573	PHASE2	TERMINATED	Efficacy of D-Cycloserine for Enhancing the Effects of CBT for Substance Use
NCT00591825	PHASE2	COMPLETED	fMRI Study Examining Effects of D-cycloserine in Specific Phobia
NCT00720759	PHASE2	COMPLETED	Improving Stroke Rehabilitation: Spacing Effect and D-cycloserine
NCT00759473	PHASE2	COMPLETED	D-Cycloserine Facilitation of Cocaine - Cue Extinction
NCT00780442	PHASE2	COMPLETED	D-Cycloserine and Cue Exposure in Cocaine-Dependent Individuals
NCT00790868	PHASE2	COMPLETED	Exposure, D-Cycloserine Enhancement, and Genetic Modulators in Panic Disorder
NCT00827281	PHASE2	WITHDRAWN	D-Cycloserine Enhancement of Exposure-Based CBT for Smoking Cessation (DCSSmoking)
NCT00864123	PHASE2	COMPLETED	D-Cycloserine Augmentation of Therapy for Pediatric Obsessive-Compulsive Disorder
NCT00869765	PHASE2	COMPLETED	Transcranial Direct Current Stimulation (tDCS) Augmentation by D-Cycloserine as a Treatment for Depression
NCT01157416	PHASE2	COMPLETED	Effect of D-cycloserine on Treatment of Posttraumatic Stress Disorder (PTSD) in Youth
NCT01157429	PHASE2	COMPLETED	D-cycloserine Adjunctive Treatment for Posttraumatic Stress Disorder (PTSD) in Adolescents
NCT01343862	PHASE2	UNKNOWN	The Effect of Single Dose D-Cycloserine on Cognitive Outcome in Moderate Traumatic Brain Injury (TBI) Patients
NCT01361633	PHASE2	COMPLETED	The Cognitive Enhancing Effects of D-Cycloserine Among Non-Demented Elderly
NCT01526538	PHASE2	COMPLETED	Improving Learning-based Treatment of Cocaine Dependence With Medication
NCT01687140	PHASE2	UNKNOWN	The Use of D-Cycloserine to Augment CBT for Pediatric OCD
NCT01907594	PHASE2	WITHDRAWN	Effects of Nicotine Replacement Therapy and D-cycloserine on Nicotine Treatment Seekers
NCT01923896	PHASE1/PHASE2	COMPLETED	D-cycloserine and Treatment of Feeding Disorders
NCT01928823	PHASE2	COMPLETED	Augmentation of Psychotherapy With D-Cycloserine in Agoraphobia
NCT02082912	PHASE2	COMPLETED	NMDA Receptors in Motor Learning in Humans
NCT02933684	PHASE2	WITHDRAWN	D-Cycloserine and Virtual Reality Exposure Therapy
NCT02983734	PHASE2	UNKNOWN	D-cycloserine: A Novel Treatment for Gulf War Illness (GWDCS)
NCT03535688	PHASE2	TERMINATED	D-cycloserine for the Treatment of Chronic, Refractory Low Back Pain
NCT03937596	PHASE2	COMPLETED	Adjunctive D-Cycloserine in Major Depressive Disorder
NCT04035603	PHASE2	WITHDRAWN	Multimodal Cue Exposure Therapy for Smoking Cessation
NCT05081986	PHASE2	COMPLETED	Repeated iTBS Cycloserine Motor Plasticity
NCT05177601	PHASE2	UNKNOWN	iTBS-DCS in Obsessive Compulsive Disorder
NCT05395494	PHASE2	TERMINATED	iTBS-DCS in Fibromyalgia
NCT05994703	PHASE2	COMPLETED	Assisting Smokers to Switch to an e-Cigarette by Accelerating Learning of Adaptive Habits Using D-cycloserine
NCT00593463	PHASE1	COMPLETED	Drug Discrimination in Methadone-Maintained Humans Study 1
NCT01062932	PHASE1	COMPLETED	Investigation of Cycloserine as a Smoking Cessation Treatment
NCT02099825	PHASE1	TERMINATED	Medication Enhanced Rapid Therapy
NCT02735694	PHASE1	TERMINATED	Cycloserine in the Treatment of Sleep Apnea
NCT02769936	PHASE1	COMPLETED	Glutamate, Learning, and Working Memory
NCT03432689	PHASE1	COMPLETED	Cycloserine rTMS Plasticity Augmentation
NCT03511599	PHASE1	COMPLETED	Cycloserine rTMS Plasticity Augmentation in Depression
NCT05731323	PHASE1	COMPLETED	D-Cycloserine+iTBS PK Study
NCT07560878	EARLY_PHASE1	RECRUITING	Synaptic Mechanisms of Continuous Theta Burst Stimulation in Depression
NCT00842309	EARLY_PHASE1	COMPLETED	D-Cycloserine Augmentation of Behavior Therapy for Individuals With Body Dysmorphic Disorder
NCT01944423	EARLY_PHASE1	COMPLETED	Enhancing Panic and Smoking Reduction Treatment With D-Cycloserine
NCT01985750	EARLY_PHASE1	UNKNOWN	Understanding the Importance of Plasticity in the Brain Mechanisms of Dyspnoea Perception
NCT02066792	EARLY_PHASE1	COMPLETED	Dose Timing of D-Cycloserine to Augment CBT for Social Anxiety Disorder
NCT02304432	EARLY_PHASE1	COMPLETED	Targeting a Genetic Mutation in Glycine Metabolism With D-cycloserine
NCT02312635	EARLY_PHASE1	UNKNOWN	Augmentation of Cognitive Training in Children With TBI With D-Cyloserine
NCT03780829	EARLY_PHASE1	TERMINATED	AIH for Spinal Cord Repair
NCT04357951	EARLY_PHASE1	WITHDRAWN	D-cycloserine Augmented Treatment for Youth With Tic Disorders
NCT07198685	Not specified	NOT_YET_RECRUITING	6 Months of Bedaquiline(BDQ), Delamanid(DLM), Linezolid(LZD) and Levofloxacin(LFX) in RR-TB Patients in Hubei Province
NCT00000796	Not specified	COMPLETED	A Prospective Study of Multidrug Resistance and a Pilot Study of the Safety of and Clinical and Microbiologic Response to Levofloxacin in Combination With Other Antimycobacterial Drugs for Treatment of Multidrug-Resistant Pulmonary Tuberculosis (MDRTB) in HIV-Infected Patients.
NCT00042289	Not specified	COMPLETED	Pharmacokinetic Study of Antiretroviral Drugs and Related Drugs During and After Pregnancy
NCT00126282	Not specified	COMPLETED	A Medication Trial Combined With Behavior Therapy for Individuals With Obsessive-compulsive Disorder
NCT00131339	Not specified	COMPLETED	Augmenting Exposure Therapy With an N-Methyl-D-Aspartate (NMDA) Agonist for Panic Disorder
NCT00371176	Not specified	COMPLETED	A Placebo-Controlled Trial of D-Cycloserine and Exposure Therapy for Combat-PTSD
NCT00632632	Not specified	COMPLETED	Virtual Reality & D-cycloserine (DCS) for Posttraumatic Stress Disorder (PTSD)
NCT00633256	Not specified	COMPLETED	The Effect of Cycloserine on Smoking Behavior in Nicotine Dependent Smokers
NCT00755820	Not specified	COMPLETED	Food Exposure Therapy in Anorexia Nervosa
NCT00855153	Not specified	WITHDRAWN	Virtual Reality and D-Cycloserine in Combat Related Psycological Trauma in Burn Service Members
NCT00963924	Not specified	COMPLETED	D-cycloserine Augmentation of Cognitive Remediation in Schizophrenia
NCT01037101	Not specified	UNKNOWN	D-Cycloserine-Enhancer of One-Session Treatment for Phobia of Heights

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).