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
Drug resistance	401.94	36.64	114	3397	22819	63462692
Viral mutation identified	389.31	36.64	70	3441	1740	63483771
Pregnancy	385.53	36.64	123	3388	36713	63448798
Virologic failure	309.94	36.64	58	3453	1804	63483707
Lipodystrophy acquired	304.63	36.64	55	3456	1397	63484114
Lactic acidosis	277.40	36.64	97	3414	38190	63447321
Immune reconstitution inflammatory syndrome	220.98	36.64	54	3457	6030	63479481
Pathogen resistance	178.56	36.64	46	3465	6352	63479159
Foetal exposure during pregnancy	160.86	36.64	62	3449	31900	63453611
Caesarean section	149.88	36.64	50	3461	16982	63468529
Abortion induced	139.67	36.64	42	3469	10200	63475311
Mitochondrial toxicity	132.64	36.64	23	3488	458	63485053
Portal hypertension	119.02	36.64	30	3481	3789	63481722
Hypertriglyceridaemia	86.74	36.64	26	3485	6233	63479278
Hyperlactacidaemia	81.96	36.64	21	3490	2828	63482683
Acquired gene mutation	80.77	36.64	17	3494	966	63484545
Pregnancy on contraceptive	77.50	36.64	17	3494	1175	63484336
Stillbirth	76.38	36.64	24	3487	6726	63478785
Abortion spontaneous	74.75	36.64	41	3470	47154	63438357
Exposure during pregnancy	73.48	36.64	64	3447	155483	63330028
Normal newborn	71.38	36.64	24	3487	8317	63477194
Premature delivery	64.21	36.64	32	3479	30249	63455262
Live birth	63.11	36.64	30	3481	25600	63459911
Fat tissue increased	63.07	36.64	13	3498	666	63484845
Lipoatrophy	59.69	36.64	11	3500	312	63485199
Blood lactic acid increased	59.10	36.64	20	3491	7066	63478445
Premature rupture of membranes	57.51	36.64	18	3493	4975	63480536
Premature baby	56.39	36.64	26	3485	20709	63464802
Dyslipidaemia	46.82	36.64	17	3494	7376	63478135
Blood HIV RNA increased	39.60	36.64	9	3502	730	63484781
Pulmonary tuberculosis	38.65	36.64	13	3498	4504	63481007
Treatment noncompliance	37.01	36.64	24	3487	37301	63448210

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	987.40	23.09	207	6668	3137	34946919
Mitochondrial toxicity	738.59	23.09	157	6718	2542	34947514
Eyelid ptosis	580.59	23.09	149	6726	5617	34944439
Immune reconstitution inflammatory syndrome	426.34	23.09	128	6747	8631	34941425
Diplopia	385.07	23.09	139	6736	16704	34933352
Progressive external ophthalmoplegia	361.22	23.09	78	6797	1357	34948699
Virologic failure	259.62	23.09	71	6804	3409	34946647
Viral mutation identified	205.22	23.09	57	6818	2897	34947159
Drug resistance	203.37	23.09	100	6775	25827	34924229
Foetal exposure during pregnancy	185.71	23.09	107	6768	37994	34912062
Pathogen resistance	153.87	23.09	61	6814	9421	34940635
Ophthalmoplegia	153.41	23.09	41	6834	1799	34948257
Blood lactic acid increased	144.10	23.09	53	6822	6675	34943381
Lipoatrophy	135.44	23.09	29	6846	482	34949574
Hypertriglyceridaemia	132.37	23.09	53	6822	8395	34941661
Osteonecrosis	112.38	23.09	56	6819	14834	34935222
Hepatic fibrosis	108.74	23.09	39	6836	4568	34945488
Lactic acidosis	88.45	23.09	65	6810	34707	34915349
Multiple-drug resistance	82.50	23.09	33	6842	5206	34944850
Kaposi's sarcoma	79.90	23.09	21	6854	862	34949194
Portal hypertension	79.63	23.09	30	6845	4032	34946024
Hyperlipidaemia	79.29	23.09	44	6831	14485	34935571
Facial wasting	71.68	23.09	14	6861	143	34949913
Hyperlactacidaemia	69.17	23.09	25	6850	2991	34947065
Dyslipidaemia	68.06	23.09	32	6843	7456	34942600
Drug-induced liver injury	62.48	23.09	49	6826	28783	34921273
Blood triglycerides increased	61.58	23.09	37	6838	14122	34935934
Off label use	53.96	23.09	9	6866	419515	34530541
Acquired gene mutation	53.93	23.09	17	6858	1338	34948718
CD4 lymphocytes decreased	53.68	23.09	18	6857	1723	34948333
Blood bilirubin unconjugated increased	52.54	23.09	14	6861	606	34949450
Premature baby	48.31	23.09	36	6839	19597	34930459
Mitochondrial myopathy	45.18	23.09	10	6865	195	34949861
Dysphagia	44.52	23.09	58	6817	62323	34887733
Progressive multifocal leukoencephalopathy	43.71	23.09	26	6849	9738	34940318
Meningitis cryptococcal	40.84	23.09	16	6859	2388	34947668
Trisomy 21	39.25	23.09	11	6864	576	34949480
Enophthalmos	38.29	23.09	6	6869	13	34950043
Cytomegalovirus chorioretinitis	37.81	23.09	17	6858	3572	34946484
Basedow's disease	36.94	23.09	7	6868	60	34949996
Treatment failure	35.79	23.09	45	6830	46652	34903404
Pinealoblastoma	35.02	23.09	8	6867	181	34949875
Hypotension	32.68	23.09	3	6872	221646	34728410
Drug ineffective	31.89	23.09	26	6849	456725	34493331
Heart transplant rejection	31.23	23.09	11	6864	1220	34948836
Pulmonary tuberculosis	30.39	23.09	16	6859	4738	34945318
Nodular regenerative hyperplasia	29.76	23.09	10	6865	963	34949093
Fanconi syndrome acquired	29.47	23.09	12	6863	1979	34948077
Fall	29.24	23.09	3	6872	202882	34747174
Hepatic cirrhosis	28.28	23.09	25	6850	17289	34932767
Lagophthalmos	28.23	23.09	6	6869	96	34949960
Neuropathy peripheral	28.12	23.09	55	6820	83208	34866848
Gynaecomastia	28.06	23.09	20	6855	10160	34939896
Low set ears	27.80	23.09	8	6867	461	34949595
Hepatomegaly	27.68	23.09	20	6855	10376	34939680
Lipohypertrophy	27.02	23.09	7	6868	271	34949785
Mycobacterium avium complex infection	26.79	23.09	12	6863	2499	34947557
Pneumocystis jirovecii pneumonia	25.51	23.09	25	6850	19685	34930371
Protrusion tongue	24.24	23.09	6	6869	193	34949863
Central pain syndrome	24.15	23.09	5	6870	70	34949986
Glucose tolerance impaired	23.65	23.09	12	6863	3292	34946764

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	1275.32	24.04	243	8560	4082	79731503
Mitochondrial toxicity	917.80	24.04	175	8628	2939	79732646
Immune reconstitution inflammatory syndrome	700.98	24.04	184	8619	13657	79721928
Eyelid ptosis	584.03	24.04	152	8651	10892	79724693
Drug resistance	480.46	24.04	179	8624	42034	79693551
Virologic failure	444.02	24.04	101	8702	4090	79731495
Progressive external ophthalmoplegia	411.71	24.04	79	8724	1366	79734219
Viral mutation identified	392.69	24.04	90	8713	3768	79731817
Diplopia	369.99	24.04	139	8664	33327	79702258
Pregnancy	283.91	24.04	108	8695	26743	79708842
Lactic acidosis	267.81	24.04	138	8665	70221	79665364
Lipoatrophy	185.90	24.04	36	8767	653	79734932
Portal hypertension	183.96	24.04	56	8747	7052	79728533
Pathogen resistance	174.57	24.04	64	8739	14278	79721307
Ophthalmoplegia	158.20	24.04	41	8762	2871	79732714
Acquired gene mutation	133.82	24.04	34	8769	2199	79733386
Hepatic fibrosis	129.04	24.04	43	8760	7237	79728348
Osteonecrosis	118.15	24.04	61	8742	31034	79704551
Abortion induced	110.30	24.04	38	8765	7071	79728514
Hyperlactacidaemia	106.99	24.04	35	8768	5560	79730025
Dyslipidaemia	105.86	24.04	42	8761	11591	79723994
Hypertriglyceridaemia	105.57	24.04	43	8760	12697	79722888
Caesarean section	102.82	24.04	42	8761	12493	79723092
CD4 lymphocytes decreased	91.16	24.04	26	8777	2608	79732977
Multiple-drug resistance	87.89	24.04	34	8769	8774	79726811
Blood lactic acid increased	85.45	24.04	37	8766	12707	79722878
Facial wasting	79.75	24.04	13	8790	81	79735504
Pulmonary tuberculosis	77.19	24.04	30	8773	7835	79727750
Neuropathy peripheral	76.70	24.04	86	8717	141219	79594366
Kaposi's sarcoma	73.42	24.04	17	8786	742	79734843
Pregnancy on contraceptive	70.26	24.04	17	8786	898	79734687
Drug-induced liver injury	69.67	24.04	58	8745	66059	79669526
Fat tissue increased	69.44	24.04	17	8786	943	79734642
Foetal exposure during pregnancy	67.34	24.04	25	8778	5765	79729820
Meningitis cryptococcal	59.31	24.04	20	8783	3486	79732099
Normal newborn	59.03	24.04	24	8779	7048	79728537
Abortion spontaneous	58.68	24.04	38	8765	29469	79706116
Blood bilirubin unconjugated increased	58.26	24.04	15	8788	1022	79734563
Hyperlipidaemia	57.86	24.04	36	8767	26057	79709528
Stillbirth	56.95	24.04	20	8783	3935	79731650
Off label use	55.21	24.04	16	8787	907199	78828386
Progressive multifocal leukoencephalopathy	54.94	24.04	32	8771	20568	79715017
Blood triglycerides increased	54.31	24.04	32	8771	21008	79714577
Nodular regenerative hyperplasia	54.22	24.04	15	8788	1346	79734239
Hepatomegaly	49.49	24.04	29	8774	18845	79716740
Pancreatitis	48.32	24.04	48	8755	68527	79667058
Mitochondrial myopathy	47.24	24.04	10	8793	287	79735298
Stevens-Johnson syndrome	46.82	24.04	37	8766	39129	79696456
Premature delivery	46.11	24.04	30	8773	23437	79712148
Dysphagia	44.69	24.04	61	8742	122075	79613510
Basedow's disease	42.84	24.04	9	8794	249	79735336
Fall	42.32	24.04	3	8800	487626	79247959
Live birth	41.91	24.04	26	8777	18718	79716867
Pain	41.69	24.04	13	8790	703789	79031796
Gynaecomastia	40.95	24.04	19	8784	7662	79727923
Tuberculoma of central nervous system	40.46	24.04	10	8793	577	79735008
Pinealoblastoma	40.38	24.04	7	8796	66	79735519
Treatment failure	39.61	24.04	69	8734	170417	79565168
Pneumocystis jirovecii pneumonia	39.48	24.04	31	8772	32477	79703108
Tuberculosis	36.32	24.04	22	8781	15176	79720409
Ascites	34.30	24.04	42	8761	75520	79660065
Treatment noncompliance	33.91	24.04	35	8768	52233	79683352
Lymphadenopathy	33.37	24.04	35	8768	53212	79682373
Hyperbilirubinaemia	33.32	24.04	25	8778	24493	79711092
Blood HIV RNA increased	33.31	24.04	11	8792	1797	79733788
Enophthalmos	33.14	24.04	6	8797	74	79735511
Mycobacterium avium complex infection	32.95	24.04	14	8789	4586	79730999
Gene mutation	32.71	24.04	12	8791	2674	79732911
Hepatosplenomegaly	32.31	24.04	15	8788	6054	79729531
Oesophageal varices haemorrhage	30.70	24.04	13	8790	4223	79731362
Hepatitis B	30.63	24.04	16	8787	8316	79727269
Cytomegalovirus chorioretinitis	30.57	24.04	14	8789	5476	79730109
Hepatic failure	29.37	24.04	35	8768	61177	79674408
Gamma-glutamyltransferase increased	29.14	24.04	33	8770	54647	79680938
Premature rupture of membranes	27.88	24.04	12	8791	4057	79731528
Immune reconstitution inflammatory syndrome associated tuberculosis	27.79	24.04	8	8795	828	79734757
Hepatic steatosis	27.66	24.04	27	8776	37711	79697874
Hepatic cirrhosis	27.52	24.04	26	8777	34880	79700705
Molluscum contagiosum	27.11	24.04	7	8796	482	79735103
Oligohydramnios	26.50	24.04	11	8792	3401	79732184
Placental insufficiency	25.47	24.04	8	8795	1115	79734470
Fanconi syndrome acquired	25.46	24.04	10	8793	2684	79732901
Drug ineffective	25.24	24.04	51	8752	1080862	78654723
Meningitis tuberculous	24.91	24.04	8	8795	1197	79734388
Liver disorder	24.72	24.04	35	8768	72382	79663203
Viral load increased	24.58	24.04	10	8793	2938	79732647
Fatigue	24.23	24.04	41	8762	929686	78805899

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
12678	IUPHAR_LIGAND_ID
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