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

Stem definition	Drug id	CAS RN
uridine derivatives used as antiviral agents and as antineoplastics	2478	3056-17-5

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: zerit stavudine sanilvudine staduvine	A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV. Molecular weight: 224.22 Formula: C10H12N2O4 CLOGP: -0.74 LIPINSKI: 0 HAC: 6 HDO: 2 TPSA: 78.87 ALOGS: -0.74 ROTB: 2 Status: OFM Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

zerit
stavudine
sanilvudine
staduvine

A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.

Molecular weight: 224.22
Formula: C10H12N2O4
CLOGP: -0.74
LIPINSKI: 0
HAC: 6
HDO: 2
TPSA: 78.87
ALOGS: -0.74
ROTB: 2

Status: OFM

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

Drug dosage:

Dose	Unit	Route
80	mg	O

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	83 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	39 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	5.95 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	82 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.67 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	8.20 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	1 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	1.40 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
June 24, 1994	FDA	BRISTOL MYERS SQUIBB

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
Pregnancy	387.99	37.45	123	3294	29454	50572253
Drug resistance	382.74	37.45	110	3307	18879	50582828
Viral mutation identified	369.81	37.45	68	3349	1561	50600146
Virologic failure	295.88	37.45	56	3361	1508	50600199
Lipodystrophy acquired	279.32	37.45	52	3365	1277	50600430
Lactic acidosis	271.57	37.45	97	3320	33258	50568449
Immune reconstitution inflammatory syndrome	215.53	37.45	54	3363	5462	50596245
Pathogen resistance	174.82	37.45	46	3371	5643	50596064
Foetal exposure during pregnancy	158.21	37.45	62	3355	27297	50574410
Caesarean section	144.29	37.45	50	3367	15589	50586118
Abortion induced	135.21	37.45	42	3375	9302	50592405
Mitochondrial toxicity	134.84	37.45	23	3394	335	50601372
Portal hypertension	116.61	37.45	30	3387	3362	50598345
Hypertriglyceridaemia	84.97	37.45	26	3391	5465	50596242
Hyperlactacidaemia	81.09	37.45	21	3396	2412	50599295
Acquired gene mutation	80.23	37.45	17	3400	814	50600893
Pregnancy on contraceptive	76.24	37.45	17	3400	1035	50600672
Stillbirth	74.63	37.45	24	3393	5928	50595779
Exposure during pregnancy	74.29	37.45	63	3354	120952	50480755
Normal newborn	71.88	37.45	24	3393	6667	50595040
Abortion spontaneous	71.78	37.45	41	3376	41731	50559976
Live birth	70.19	37.45	30	3387	16378	50585329
Premature delivery	65.64	37.45	32	3385	23631	50578076
Fat tissue increased	62.78	37.45	13	3404	556	50601151
Blood lactic acid increased	59.85	37.45	20	3397	5565	50596142
Lipoatrophy	57.84	37.45	11	3406	302	50601405
Premature rupture of membranes	55.51	37.45	18	3399	4562	50597145
Premature baby	54.48	37.45	26	3391	18311	50583396
Blood HIV RNA increased	40.48	37.45	9	3408	540	50601167

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
Lipodystrophy acquired	906.84	22.46	195	6479	2899	29564954
Mitochondrial toxicity	678.23	22.46	147	6527	2264	29565589
Eyelid ptosis	527.64	22.46	139	6535	5047	29562806
Immune reconstitution inflammatory syndrome	410.73	22.46	125	6549	7677	29560176
Diplopia	358.29	22.46	129	6545	13389	29554464
Progressive external ophthalmoplegia	323.96	22.46	72	6602	1245	29566608
Virologic failure	231.43	22.46	64	6610	2783	29565070
Foetal exposure during pregnancy	183.77	22.46	107	6567	33760	29534093
Drug resistance	181.02	22.46	91	6583	21449	29546404
Blood lactic acid increased	137.58	22.46	51	6623	5715	29562138
Ophthalmoplegia	132.93	22.46	37	6637	1645	29566208
Lipoatrophy	132.74	22.46	29	6645	460	29567393
Hypertriglyceridaemia	131.60	22.46	53	6621	7422	29560431
Viral mutation identified	127.06	22.46	39	6635	2449	29565404
Hepatic fibrosis	112.82	22.46	38	6636	3214	29564639
Osteonecrosis	110.22	22.46	56	6618	13463	29554390
Pathogen resistance	101.04	22.46	45	6629	8071	29559782
Lactic acidosis	88.57	22.46	65	6609	30182	29537671
Portal hypertension	80.09	22.46	30	6644	3456	29564397
Hyperlipidaemia	79.53	22.46	44	6630	12546	29555307
Kaposi's sarcoma	77.54	22.46	21	6653	841	29567012
Dyslipidaemia	70.32	22.46	32	6642	6029	29561824
Facial wasting	70.30	22.46	14	6660	137	29567716
Hyperlactacidaemia	68.71	22.46	25	6649	2653	29565200
Drug-induced liver injury	66.69	22.46	48	6626	21607	29546246
Blood triglycerides increased	60.24	22.46	37	6637	12797	29555056
Acquired gene mutation	52.88	22.46	17	6657	1241	29566612
CD4 lymphocytes decreased	52.77	22.46	18	6656	1580	29566273
Blood bilirubin unconjugated increased	52.07	22.46	14	6660	545	29567308
Premature baby	47.99	22.46	36	6638	17244	29550609
Off label use	47.61	22.46	6	6668	300794	29267059
Mitochondrial myopathy	43.86	22.46	10	6664	194	29567659
Dysphagia	40.99	22.46	56	6618	54870	29512983
Meningitis cryptococcal	40.80	22.46	16	6658	2084	29565769
Progressive multifocal leukoencephalopathy	40.56	22.46	25	6649	8694	29559159
Multiple-drug resistance	40.28	22.46	19	6655	3881	29563972
Trisomy 21	39.35	22.46	11	6663	496	29567357
Enophthalmos	37.47	22.46	6	6668	13	29567840
Basedow's disease	36.09	22.46	7	6667	59	29567794
Pinealoblastoma	34.18	22.46	8	6666	175	29567678
Hypotension	32.94	22.46	3	6671	194351	29373502
Nodular regenerative hyperplasia	31.89	22.46	10	6664	673	29567180
Treatment failure	31.14	22.46	40	6634	36899	29530954
Cytomegalovirus chorioretinitis	31.07	22.46	15	6659	3223	29564630
Heart transplant rejection	30.47	22.46	11	6663	1140	29566713
Pulmonary tuberculosis	29.78	22.46	16	6658	4299	29563554
Gynaecomastia	29.44	22.46	20	6654	8197	29559656
Fall	29.32	22.46	3	6671	177175	29390678
Hepatic cirrhosis	29.23	22.46	25	6649	14419	29553434
Fanconi syndrome acquired	28.78	22.46	12	6662	1830	29566023
Lipohypertrophy	27.76	22.46	7	6667	211	29567642
Lagophthalmos	27.52	22.46	6	6668	94	29567759
Low set ears	27.27	22.46	8	6666	429	29567424
Hepatomegaly	27.18	22.46	20	6654	9297	29558556
Neuropathy peripheral	26.52	22.46	53	6621	70974	29496879
Mycobacterium avium complex infection	26.37	22.46	12	6662	2257	29565596
Drug ineffective	26.34	22.46	26	6648	363144	29204709
Pneumocystis jirovecii pneumonia	26.01	22.46	25	6649	16754	29551099
Glucose tolerance impaired	23.99	22.46	12	6662	2782	29565071
Protrusion tongue	23.69	22.46	6	6668	184	29567669
Central pain syndrome	23.66	22.46	5	6669	67	29567786
Atypical mycobacterial infection	23.55	22.46	8	6666	693	29567160

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
Lipodystrophy acquired	1173.56	23.73	231	8367	3796	64486338
Mitochondrial toxicity	847.67	23.73	165	8433	2541	64487593
Immune reconstitution inflammatory syndrome	680.92	23.73	183	8415	12287	64477847
Eyelid ptosis	530.25	23.73	142	8456	9383	64480751
Drug resistance	439.82	23.73	168	8430	34934	64455200
Virologic failure	417.30	23.73	96	8502	3370	64486764
Progressive external ophthalmoplegia	367.14	23.73	73	8525	1254	64488880
Diplopia	338.32	23.73	129	8469	26636	64463498
Viral mutation identified	335.97	23.73	80	8518	3266	64486868
Pregnancy	290.62	23.73	108	8490	20757	64469377
Lactic acidosis	260.99	23.73	138	8460	61272	64428862
Lipoatrophy	181.50	23.73	36	8562	609	64489525
Portal hypertension	180.93	23.73	56	8542	6163	64483971
Pathogen resistance	149.55	23.73	58	8540	12485	64477649
Ophthalmoplegia	134.82	23.73	37	8561	2665	64487469
Acquired gene mutation	131.41	23.73	34	8564	1952	64488182
Hepatic fibrosis	124.43	23.73	41	8557	5511	64484623
Osteonecrosis	112.88	23.73	61	8537	28168	64461966
Abortion induced	107.27	23.73	38	8560	6350	64483784
Hyperlactacidaemia	105.46	23.73	35	8563	4809	64485325
Dyslipidaemia	104.03	23.73	41	8557	9201	64480933
Hypertriglyceridaemia	103.07	23.73	43	8555	11162	64478972
Caesarean section	99.47	23.73	42	8556	11232	64478902
CD4 lymphocytes decreased	88.33	23.73	26	8572	2409	64487725
Blood lactic acid increased	79.45	23.73	35	8563	10366	64479768
Facial wasting	77.72	23.73	13	8585	78	64490056
Pulmonary tuberculosis	74.10	23.73	30	8568	7214	64482920
Neuropathy peripheral	73.00	23.73	84	8514	117441	64372693
Drug-induced liver injury	72.39	23.73	56	8542	47587	64442547
Kaposi's sarcoma	70.45	23.73	17	8581	732	64489402
Multiple-drug resistance	70.22	23.73	28	8570	6474	64483660
Pregnancy on contraceptive	69.53	23.73	17	8581	774	64489360
Foetal exposure during pregnancy	69.01	23.73	25	8573	4451	64485683
Fat tissue increased	68.45	23.73	17	8581	826	64489308
Normal newborn	60.00	23.73	24	8574	5593	64484541
Meningitis cryptococcal	58.61	23.73	20	8578	2989	64487145
Nodular regenerative hyperplasia	58.07	23.73	15	8583	855	64489279
Abortion spontaneous	57.69	23.73	38	8560	25105	64465029
Blood bilirubin unconjugated increased	57.28	23.73	15	8583	902	64489232
Hyperlipidaemia	55.84	23.73	36	8562	22940	64467194
Stillbirth	54.92	23.73	20	8578	3613	64486521
Blood triglycerides increased	51.96	23.73	32	8566	18834	64471300
Progressive multifocal leukoencephalopathy	50.40	23.73	31	8567	18201	64471933
Live birth	49.81	23.73	26	8572	11178	64478956
Hepatomegaly	47.42	23.73	29	8569	16853	64473281
Off label use	47.34	23.73	13	8585	632793	63857341
Premature delivery	47.33	23.73	30	8568	18559	64471575
Pancreatitis	46.37	23.73	48	8550	59559	64430575
Mitochondrial myopathy	45.64	23.73	10	8588	279	64489855
Fall	43.97	23.73	3	8595	416823	64073311
Gynaecomastia	41.96	23.73	19	8579	5997	64484137
Basedow's disease	41.28	23.73	9	8589	245	64489889
Stevens-Johnson syndrome	40.91	23.73	35	8563	34214	64455920
Dysphagia	39.23	23.73	59	8539	106753	64383381
Tuberculoma of central nervous system	39.16	23.73	10	8588	544	64489590
Pinealoblastoma	39.06	23.73	7	8591	66	64490068
Pneumocystis jirovecii pneumonia	38.76	23.73	31	8567	27603	64462531
Pain	38.43	23.73	13	8585	553498	63936636
Treatment failure	37.98	23.73	61	8537	116755	64373379
Tuberculosis	35.60	23.73	22	8576	13016	64477118
Ascites	34.61	23.73	42	8556	61959	64428175
Gene mutation	33.49	23.73	12	8586	2070	64488064
Blood HIV RNA increased	33.41	23.73	11	8587	1473	64488661
Mycobacterium avium complex infection	32.50	23.73	14	8584	3926	64486208
Enophthalmos	32.48	23.73	6	8592	68	64490066
Lymphadenopathy	31.72	23.73	35	8563	46651	64443483
Hepatosplenomegaly	31.44	23.73	15	8583	5328	64484806
Oesophageal varices haemorrhage	30.28	23.73	13	8585	3616	64486518
Hyperbilirubinaemia	30.19	23.73	24	8574	21181	64468953
Hepatic cirrhosis	29.63	23.73	26	8572	26272	64463862
Cytomegalovirus chorioretinitis	29.54	23.73	14	8584	4898	64485236
Hepatitis B	28.90	23.73	16	8582	7729	64482405
Hepatic steatosis	27.84	23.73	27	8571	30980	64459154
Gamma-glutamyltransferase increased	27.29	23.73	33	8565	48477	64441657
Immune reconstitution inflammatory syndrome associated tuberculosis	26.92	23.73	8	8590	765	64489369
Hepatic failure	26.89	23.73	35	8563	55359	64434775
Premature rupture of membranes	26.67	23.73	12	8586	3732	64486402
Molluscum contagiosum	26.26	23.73	7	8591	451	64489683
Oligohydramnios	25.44	23.73	11	8587	3113	64487021
Treatment noncompliance	25.15	23.73	30	8568	43452	64446682
Liver disorder	24.80	23.73	33	8565	53318	64436816
Placental insufficiency	24.74	23.73	8	8590	1012	64489122
Fanconi syndrome acquired	24.66	23.73	10	8588	2411	64487723
Hypotension	24.63	23.73	10	8588	380964	64109170
Viral load increased	24.40	23.73	10	8588	2477	64487657
Fatigue	24.38	23.73	39	8559	748691	63741443
Meningitis tuberculous	24.07	23.73	8	8590	1103	64489031

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	J05AF04	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Nucleoside and nucleotide reverse transcriptase inhibitors
ATC	J05AR07	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
FDA MoA	N0000009947	Nucleoside Reverse Transcriptase Inhibitors
FDA EXT	N0000175459	Nucleoside Analog
FDA EPC	N0000175462	Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor
CHEBI has role	CHEBI:22587	antiviral agents
CHEBI has role	CHEBI:35221	antimetabolite
CHEBI has role	CHEBI:59897	reverse transcriptase inhibitors
MeSH PA	D019380	Anti-HIV Agents
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D044966	Anti-Retroviral Agents
MeSH PA	D000963	Antimetabolites
MeSH PA	D000998	Antiviral Agents
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D009676	Noxae
MeSH PA	D019384	Nucleic Acid Synthesis Inhibitors
MeSH PA	D018894	Reverse Transcriptase Inhibitors

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

Disease	Relation	SNOMED_ID	DOID
Human immunodeficiency virus infection	indication	86406008	DOID:526
Prevention of HIV Infection after Exposure	off-label use
Alcoholism	contraindication	7200002
Diabetes mellitus	contraindication	73211009	DOID:9351
Hyperglycemia	contraindication	80394007	DOID:4195
Kidney disease	contraindication	90708001	DOID:557
Lactic acidosis	contraindication	91273001	DOID:3650
Steatosis of liver	contraindication	197321007
Acute pancreatitis	contraindication	197456007	DOID:2913
Chronic pancreatitis	contraindication	235494005
Disease of liver	contraindication	235856003	DOID:409
Peripheral nerve disease	contraindication	302226006
Breastfeeding (mother)	contraindication	413712001
Obesity	contraindication	414916001	DOID:9970

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.3	acidic
pKa2	13.25	acidic

Orange Book patent data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
100MG	ZERIT XR	BRISTOL MYERS SQUIBB	N021453	Dec. 31, 2002	DISCN	CAPSULE, EXTENDED RELEASE	ORAL	7135465	Feb. 18, 2023	METHOD FOR TREATING HIV-1 INFECTION
37.5MG	ZERIT XR	BRISTOL MYERS SQUIBB	N021453	Dec. 31, 2002	DISCN	CAPSULE, EXTENDED RELEASE	ORAL	7135465	Feb. 18, 2023	METHOD FOR TREATING HIV-1 INFECTION
50MG	ZERIT XR	BRISTOL MYERS SQUIBB	N021453	Dec. 31, 2002	DISCN	CAPSULE, EXTENDED RELEASE	ORAL	7135465	Feb. 18, 2023	METHOD FOR TREATING HIV-1 INFECTION
75MG	ZERIT XR	BRISTOL MYERS SQUIBB	N021453	Dec. 31, 2002	DISCN	CAPSULE, EXTENDED RELEASE	ORAL	7135465	Feb. 18, 2023	METHOD FOR TREATING HIV-1 INFECTION

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Reverse transcriptase/RNaseH	Enzyme	Q72547_9HIV1	INHIBITOR	EC50	7.30	CHEMBL	CHEMBL
Gag-Pol polyprotein	Polyprotein	POL_HV1A2				WOMBAT-PK
Reverse transcriptase	Enzyme	Q9WKE8_9HIV1		IC50	7.22	CHEMBL

External reference:

ID	Source
D00445	KEGG_DRUG
4020865	VANDF
C0164662	UMLSCUI
CHEBI:63581	CHEBI
CHEMBL991	ChEMBL_ID
DB00649	DRUGBANK_ID
D018119	MESH_DESCRIPTOR_UI
18283	PUBCHEM_CID
6775	INN_ID
BO9LE4QFZF	UNII
203748	RXNORM
1468	MMSL
159782	MMSL
5512	MMSL
d03773	MMSL
004502	NDDF
108690008	SNOMEDCT_US
386895008	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Stavudine	HUMAN PRESCRIPTION DRUG LABEL	1	31722-515	CAPSULE	15 mg	ORAL	ANDA	25 sections
Stavudine	HUMAN PRESCRIPTION DRUG LABEL	1	31722-516	CAPSULE	20 mg	ORAL	ANDA	25 sections
Stavudine	HUMAN PRESCRIPTION DRUG LABEL	1	31722-517	CAPSULE	30 mg	ORAL	ANDA	25 sections
Stavudine	HUMAN PRESCRIPTION DRUG LABEL	1	31722-518	CAPSULE	40 mg	ORAL	ANDA	25 sections
stavudine	HUMAN PRESCRIPTION DRUG LABEL	1	53104-0111	FOR SOLUTION	1 mg	ORAL	ANDA	26 sections
Stavudine	HUMAN PRESCRIPTION DRUG LABEL	1	53808-0594	CAPSULE	40 mg	ORAL	ANDA	25 sections
Stavudine	HUMAN PRESCRIPTION DRUG LABEL	1	53808-0595	CAPSULE	40 mg	ORAL	ANDA	25 sections
ZERIT	HUMAN PRESCRIPTION DRUG LABEL	1	53808-0656	CAPSULE, GELATIN COATED	20 mg	ORAL	NDA	24 sections
ZERIT	HUMAN PRESCRIPTION DRUG LABEL	1	53808-0657	CAPSULE, GELATIN COATED	30 mg	ORAL	NDA	24 sections
ZERIT	HUMAN PRESCRIPTION DRUG LABEL	1	53808-0795	CAPSULE, GELATIN COATED	40 mg	ORAL	NDA	24 sections
Stavudine	HUMAN PRESCRIPTION DRUG LABEL	1	53808-0852	CAPSULE	20 mg	ORAL	ANDA	30 sections