Tox | Related Drugs | BioActivity |

Stem definition	Drug id	CAS RN
antivirals phosphonic acid derivatives	2592	147127-20-6

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: tenofovir hydrate tenofovir tenefovir	An adenine analog REVERSE TRANSCRIPTASE INHIBITOR with antiviral activity against HIV-1 and HEPATITIS B. It is used to treat HIV INFECTIONS and CHRONIC HEPATITIS B, in combination with other ANTIVIRAL AGENTS, due to the emergence of ANTIVIRAL DRUG RESISTANCE when it is used alone. Molecular weight: 287.22 Formula: C9H14N5O4P CLOGP: -1.16 LIPINSKI: 0 HAC: 9 HDO: 3 TPSA: 136.38 ALOGS: -2.19 ROTB: 5 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

tenofovir hydrate
tenofovir
tenefovir

An adenine analog REVERSE TRANSCRIPTASE INHIBITOR with antiviral activity against HIV-1 and HEPATITIS B. It is used to treat HIV INFECTIONS and CHRONIC HEPATITIS B, in combination with other ANTIVIRAL AGENTS, due to the emergence of ANTIVIRAL DRUG RESISTANCE when it is used alone.

Molecular weight: 287.22
Formula: C9H14N5O4P
CLOGP: -1.16
LIPINSKI: 0
HAC: 9
HDO: 3
TPSA: 136.38
ALOGS: -2.19
ROTB: 5

Status: OFP

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

Drug dosage:

None

ADMET properties:

Property	Value	Reference
BA (Bioavailability)	25 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.83 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	3.10 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.93 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	5.80 hours	Lombardo F, Berellini G, Obach RS
S (Water solubility)	2 mg/mL	Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Bocci G, Oprea TI, Benet LZ

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Property	Description	Value	Unit	Confidence	Similarity
azlogd74	LogD at pH 7.4	-2.177		High	1
caco2-efflux	Caco-2 efflux ratio (BA/AB)	1.945		High	1
caco2-intrinsic-papp	Caco-2 intrinsic apparent permeability	0.195	10^-6 cm/s	High	1
dh-clint	Dog hepatocyte intrinsic clearance	3.776	uL/min/10^6 cells	High	1
dppb	Dog plasma protein binding (% unbound)	37.280	%	High	1
fcs-ppb	Fetal calf serum protein binding (% unbound)	52.590	%	High	1
herg	hERG pIC50	4.464	pIC50	High	1
hh-clint	Human hepatocyte intrinsic clearance	1.770	uL/min/10^6 cells	High	1
hlm-clint	Human liver microsomal intrinsic clearance	3.342	uL/min/mg protein	High	1
hppb	Human plasma protein binding (% unbound)	27.360	%	High	1
kinase-safety-class	ACVR2B,AURKA,AXL,BRAF,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,ERBB2,FLT3,GRK2,ITK,MAP2K6,MAP3K21,MAPK7,NTRK1,NTRK2,PDK1,PDK2,PIK3CD,PRKDC,SIK2,STK33,TEK	26
kinase-selectivity-class	AXL,CDK9,ERBB2,GRK2,MAP2K6,MAP3K21,PIK3CD	7
mdck-mdr1-efflux	MDCK-MDR1 efflux ratio	0.333		High	1
mh-clint	Mouse hepatocyte intrinsic clearance	5.152		High	1
mppb	Mouse plasma protein binding (% unbound)	84.510		High	1
nih-mdck-mdr1-efflux	NIH MDCK-MDR1 efflux ratio	0.256		High	1
pfas-class	PFAS structural alert (1 = True, 0 = False)	0
pld-class	Phospholipidosis risk class (1 = positive, 0 = negative)	0		High	1
pppb	Pig plasma protein binding (% unbound)	42.800	%	High	1
rh-clint	Rat hepatocyte intrinsic clearance	2.460	uL/min/10^6 cells	High	1
rh-fuinc	Rat hepatocyte fraction unbound in incubation	92.860	%	High	1
rppb	Rat plasma protein binding (% unbound)	64.220	%	High	1
solubility-dd	Solubility at pH 7.4 in DMSO	862.979	uM	High	1

Approvals:

Date	Agency	Company	Orphan
Nov. 5, 2009	FDA	HETERO DRUGS LTD
March 25, 2004	PMDA	Japan Tobacco Inc.

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
Maternal exposure during pregnancy	190.14	29.38	133	3176	359930	90265208
Drug interaction	159.54	29.38	108	3201	276345	90348793
Virologic failure	147.58	29.38	30	3279	2194	90622944
Drug resistance	134.18	29.38	48	3261	30401	90594737
Fanconi syndrome acquired	126.04	29.38	24	3285	1250	90623888
Foetal exposure during pregnancy	125.00	29.38	50	3259	42925	90582213
Immune reconstitution inflammatory syndrome	118.06	29.38	31	3278	6988	90618150
Viral mutation identified	109.18	29.38	23	3286	2002	90623136
Rebound effect	104.65	29.38	30	3279	9354	90615784
Abortion spontaneous	88.64	29.38	42	3267	54014	90571124
Exposure during pregnancy	87.31	29.38	71	3238	238339	90386799
Hepatitis B	85.88	29.38	22	3287	4497	90620641
Fanconi syndrome	76.26	29.38	17	3292	1926	90623212
Pathogen resistance	64.60	29.38	20	3289	8095	90617043
Hypophosphataemic osteomalacia	59.97	29.38	10	3299	241	90624897
Blood HIV RNA increased	59.92	29.38	12	3297	812	90624326
Hepatitis B reactivation	59.43	29.38	16	3293	3958	90621180
Premature delivery	57.10	29.38	28	3281	38734	90586404
Autoimmune hepatitis	55.86	29.38	19	3290	10332	90614806
Treatment noncompliance	52.21	29.38	29	3280	51698	90573440
Congenital umbilical hernia	50.41	29.38	9	3300	327	90624811
Birth mark	48.94	29.38	8	3301	170	90624968
Immune reconstitution inflammatory syndrome associated tuberculosis	46.78	29.38	9	3300	494	90624644
Renal tubular dysfunction	46.60	29.38	9	3300	504	90624634
Portal hypertension	43.45	29.38	13	3296	4688	90620450
Hypophosphataemia	42.15	29.38	17	3292	14837	90610301
Caesarean section	41.74	29.38	18	3291	18559	90606579
Hydrops foetalis	39.06	29.38	8	3301	605	90624533
Ergot poisoning	38.74	29.38	6	3303	89	90625049
Stillbirth	37.58	29.38	13	3296	7430	90617708
Glycosuria	37.34	29.38	9	3300	1433	90623705
Glucocorticoids increased	37.05	29.38	6	3303	120	90625018
Nephropathy toxic	34.21	29.38	14	3295	12674	90612464
Ultrasound antenatal screen	33.55	29.38	6	3303	220	90624918
Pregnancy on contraceptive	33.11	29.38	8	3301	1287	90623851
Tetany	32.13	29.38	9	3300	2575	90622563
Abortion induced	31.65	29.38	13	3296	11875	90613263

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
Psychiatric decompensation	382.66	20.89	96	6619	4126	42610494
Depression suicidal	325.22	20.89	80	6635	3165	42611455
Tearfulness	319.21	20.89	80	6635	3420	42611200
Immune reconstitution inflammatory syndrome	283.09	20.89	92	6623	10051	42604569
Depressive symptom	272.85	20.89	72	6643	3781	42610839
Psychomotor skills impaired	238.02	20.89	69	6646	5135	42609485
Lipodystrophy acquired	227.77	20.89	61	6654	3389	42611231
Paranoia	209.79	20.89	80	6635	13946	42600674
Drug interaction	203.75	20.89	229	6486	266770	42347850
Psychotic disorder	176.80	20.89	88	6627	29120	42585500
Mitochondrial toxicity	166.76	20.89	45	6670	2570	42612050
Progressive external ophthalmoplegia	157.70	20.89	38	6677	1373	42613247
Eyelid ptosis	152.20	20.89	52	6663	6609	42608011
Retinal toxicity	146.84	20.89	30	6685	497	42614123
Suicidal ideation	133.29	20.89	87	6628	48074	42566546
Hepatitis B	132.55	20.89	47	6668	6664	42607956
Psychomotor retardation	118.98	20.89	39	6676	4360	42610260
Acquired gene mutation	114.07	20.89	30	6685	1550	42613070
Fanconi syndrome acquired	106.04	20.89	30	6685	2040	42612580
Foetal exposure during pregnancy	103.64	20.89	74	6641	47237	42567383
Drug resistance	95.01	20.89	62	6653	34186	42580434
Pathogen resistance	88.99	20.89	41	6674	11409	42603211
Anxiety	77.00	20.89	94	6621	118466	42496154
Diplopia	72.03	20.89	43	6672	20273	42594347
Hepatic failure	64.28	20.89	51	6664	38049	42576571
Ophthalmoplegia	57.45	20.89	19	6696	2181	42612439
Ultrasound antenatal screen	56.94	20.89	14	6701	550	42614070
Gene mutation	53.07	20.89	17	6698	1764	42612856
Trisomy 18	51	20.89	14	6701	851	42613769
Hydrops foetalis	50.37	20.89	14	6701	891	42613729
Cleft lip and palate	49.97	20.89	14	6701	918	42613702
Fanconi syndrome	48.88	20.89	16	6699	1778	42612842
Meningitis cryptococcal	46.43	20.89	18	6697	3265	42611355
Depression	46.01	20.89	71	6644	111292	42503328
Birth mark	43.34	20.89	9	6706	162	42614458
Volvulus	43.18	20.89	15	6700	1998	42612622
Congenital umbilical hernia	41.90	20.89	10	6705	346	42614274
Hepatitis B reactivation	40.65	20.89	18	6697	4560	42610060
Drug-induced liver injury	39.92	20.89	39	6676	38234	42576386
Night blindness	39.48	20.89	9	6706	254	42614366
Adrenal suppression	36.26	20.89	11	6704	954	42613666
Nephropathy toxic	36.04	20.89	26	6689	16812	42597808
Superior mesenteric artery syndrome	35.29	20.89	7	6708	99	42614521
Treatment noncompliance	34.90	20.89	36	6679	37636	42576984
Portal hypertension	33.65	20.89	16	6699	4771	42609849
Hepatocellular carcinoma	30.74	20.89	18	6697	8176	42606444
Virologic failure	30.07	20.89	14	6701	3980	42610640
Hepatic encephalopathy	29.85	20.89	23	6692	16419	42598201
Secondary syphilis	29.61	20.89	6	6709	95	42614525
Osteomalacia	28.66	20.89	9	6706	875	42613745
Brachydactyly	25.41	20.89	6	6709	198	42614422
Renal tubular dysfunction	25.16	20.89	7	6708	447	42614173
Viral mutation identified	23.00	20.89	11	6704	3320	42611300
Hepatic fibrosis	21.77	20.89	12	6703	4860	42609760
Floppy eyelid syndrome	21.63	20.89	4	6711	38	42614582
Segmented hyalinising vasculitis	21.18	20.89	4	6711	43	42614577

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
Immune reconstitution inflammatory syndrome	449.32	21.50	127	9294	16099	110563779
Psychiatric decompensation	395.61	21.50	93	9328	5672	110574206
Drug interaction	343.62	21.50	306	9115	499877	110080001
Depression suicidal	331.92	21.50	78	9343	4746	110575132
Tearfulness	298.81	21.50	78	9343	7317	110572561
Depressive symptom	260.88	21.50	72	9349	8342	110571536
Psychomotor skills impaired	249.63	21.50	67	9354	6991	110572887
Lipodystrophy acquired	238.40	21.50	59	9362	4465	110575413
Hepatitis B	238.01	21.50	69	9352	9543	110570335
Paranoia	213.73	21.50	78	9343	22296	110557582
Psychotic disorder	184.58	21.50	89	9332	50848	110529030
Progressive external ophthalmoplegia	180.69	21.50	38	9383	1382	110578496
Mitochondrial toxicity	179.46	21.50	44	9377	3201	110576677
Fanconi syndrome acquired	177.27	21.50	43	9378	2991	110576887
Drug resistance	176.02	21.50	89	9332	56285	110523593
Retinal toxicity	174.80	21.50	38	9383	1621	110578257
Pathogen resistance	162.80	21.50	60	9361	17612	110562266
Eyelid ptosis	144.32	21.50	51	9370	13276	110566602
Acquired gene mutation	135.49	21.50	34	9387	2720	110577158
Fanconi syndrome	127.22	21.50	34	9387	3485	110576393
Suicidal ideation	121.80	21.50	84	9337	93853	110486025
Psychomotor retardation	112.50	21.50	37	9384	7755	110572123
Viral mutation identified	106.17	21.50	31	9390	4388	110575490
Virologic failure	102.68	21.50	31	9390	4921	110574957
Hepatitis B reactivation	97.93	21.50	33	9388	7451	110572427
Maternal exposure during pregnancy	92.25	21.50	111	9310	254772	110325106
Ultrasound antenatal screen	90.43	21.50	19	9402	687	110579191
Rebound effect	82.63	21.50	35	9386	14771	110565107
Hydrops foetalis	77.32	21.50	17	9404	764	110579114
Treatment noncompliance	75.65	21.50	57	9364	72933	110506945
Trisomy 18	69.78	21.50	15	9406	606	110579272
Hepatic failure	67.53	21.50	52	9369	68687	110511191
Cleft lip and palate	67.32	21.50	15	9406	717	110579161
Diplopia	65.20	21.50	42	9379	41852	110538026
Hypophosphataemic osteomalacia	63.17	21.50	13	9408	424	110579454
Abortion spontaneous	62.49	21.50	38	9383	34244	110545634
Nephropathy toxic	62.07	21.50	35	9386	27443	110552435
Gene mutation	60.64	21.50	19	9402	3410	110576468
Portal hypertension	60.40	21.50	24	9397	8613	110571265
Meningitis cryptococcal	58.39	21.50	20	9401	4742	110575136
Ophthalmoplegia	55.87	21.50	18	9403	3532	110576346
CSF HIV escape syndrome	53.84	21.50	11	9410	346	110579532
Blood HIV RNA increased	51.02	21.50	15	9406	2173	110577705
Foetal exposure during pregnancy	49.52	21.50	20	9401	7485	110572393
Hepatic encephalopathy	48.13	21.50	30	9391	28226	110551652
Anxiety	47.25	21.50	96	9325	344982	110234896
Adrenal suppression	45.65	21.50	13	9408	1683	110578195
Renal tubular dysfunction	43.83	21.50	11	9410	879	110578999
Night blindness	42.67	21.50	10	9411	599	110579279
Immune reconstitution inflammatory syndrome associated tuberculosis	41.99	21.50	11	9410	1043	110578835
Osteomalacia	41.97	21.50	12	9409	1575	110578303
Hypophosphataemia	41.38	21.50	29	9392	33153	110546725
Glycosuria	40.02	21.50	13	9408	2617	110577261
Drug-induced liver injury	39.66	21.50	50	9371	120017	110459861
Hepatocellular carcinoma	37.99	21.50	18	9403	9862	110570016
Caesarean section	35.04	21.50	19	9402	13798	110566080
Exposure during pregnancy	34.95	21.50	56	9365	167368	110412510
Superior mesenteric artery syndrome	34.39	21.50	7	9414	216	110579662
Secondary syphilis	32.84	21.50	6	9415	103	110579775
Glucocorticoids increased	31.88	21.50	6	9415	122	110579756
Ergot poisoning	31.47	21.50	6	9415	131	110579747
Autoimmune hepatitis	31.13	21.50	18	9403	14786	110565092
Malaise	29.91	21.50	10	9411	671809	109908069
Renal impairment	27.64	21.50	54	9367	188391	110391487
Hereditary optic atrophy	27.25	21.50	5	9416	88	110579790
Joint swelling	27.20	21.50	3	9418	442842	110137036
Pain	27.02	21.50	25	9396	954930	109624948
Renal tubular acidosis	25.82	21.50	11	9410	4704	110575174
Renal tubular necrosis	25.52	21.50	21	9400	30454	110549424
Hepatic cirrhosis	25.30	21.50	30	9391	67596	110512282
Depression	24.69	21.50	71	9350	317264	110262614
Acute kidney injury	24.48	21.50	113	9308	635317	109944561
Acute hepatic failure	24.19	21.50	22	9399	36446	110543432
Floppy eyelid syndrome	24.08	21.50	4	9417	38	110579840
Pregnancy on contraceptive	23.89	21.50	7	9414	1001	110578877
Lactic acidosis	23.54	21.50	34	9387	92777	110487101
Hepatitis C	23.07	21.50	14	9407	12559	110567319
Hepatic fibrosis	23.02	21.50	12	9409	8054	110571824
Cerebral toxoplasmosis	22.91	21.50	9	9412	3133	110576745
Drug level increased	22.70	21.50	24	9397	47695	110532183
Viral load increased	22.25	21.50	9	9412	3381	110576497
HIV infection	22.12	21.50	7	9414	1296	110578582
Tetany	21.71	21.50	9	9412	3595	110576283
Interstitial granulomatous dermatitis	21.51	21.50	5	9416	289	110579589

FDA Adverse Event Reporting System (Pediatric)

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
Volvulus	41.95	32.16	8	12	104	113829

Pharmacologic Action:

Source	Code	Description
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D000998	Antiviral Agents
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D018894	Reverse Transcriptase Inhibitors
MeSH PA	D019380	Anti-HIV Agents
MeSH PA	D019384	Nucleic Acid Synthesis Inhibitors
CHEBI has role	CHEBI:36044	antiviral drug
CHEBI has role	CHEBI:53756	HIV-1 reverse transcriptase inhibitor

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

Disease	Relation	SNOMED_ID	DOID
Chronic type B viral hepatitis	indication	61977001
Human immunodeficiency virus infection	indication	86406008	DOID:526
Coronavirus infection	off-label use	186747009
Prevention of HIV Infection after Exposure	off-label use
Osteomalacia	contraindication	4598005	DOID:10573
Hypophosphatemia	contraindication	4996001
Suicidal thoughts	contraindication	6471006
Hypercholesterolemia	contraindication	13644009
Torsades de pointes	contraindication	31722008
Depressive disorder	contraindication	35489007
Fanconi syndrome	contraindication	40488004	DOID:1062
Acute nephropathy	contraindication	58574008
Hepatic failure	contraindication	59927004
Aggressive behavior	contraindication	61372001
Kidney disease	contraindication	90708001	DOID:557
Lactic acidosis	contraindication	91273001	DOID:3650
Prolonged QT interval	contraindication	111975006
Chronic hepatitis C	contraindication	128302006
Seizure disorder	contraindication	128613002
Liver function tests abnormal	contraindication	166603001
Paranoid disorder	contraindication	191667009
Steatosis of liver	contraindication	197321007
Mania	contraindication	231494001
Disease of liver	contraindication	235856003	DOID:409
Pathological fracture	contraindication	268029009
Pregnancy, function	contraindication	289908002
Hypertriglyceridemia	contraindication	302870006
Severe depression	contraindication	310497006
Osteopenia	contraindication	312894000
Breastfeeding (mother)	contraindication	413712001
Obesity	contraindication	414916001	DOID:9970
Congenital long QT syndrome	contraindication	442917000

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	0.23	acidic
pKa2	4.92	acidic
pKa3	4.28	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	UniProt	Type	Activity value (-log[M])	Bioact source
Reverse transcriptase	Enzyme	Q9WKE8_9HIV1	IC50	6.42	CHEMBL
Reverse transcriptase/RNaseH	Enzyme	Q72547_9HIV1	IC50	6.42	CHEMBL
Capsid protein	Structural	Q03732_HBV	EC50	6.62	CHEMBL

External reference:

ID	Source
4021279	VUID
N0000148716	NUI
D06074	KEGG_DRUG
4021279	VANDF
C0384228	UMLSCUI
CHEBI:63716	CHEBI
TFO	PDB_CHEM_ID
CHEMBL3989702	ChEMBL_ID
DB14126	DRUGBANK_ID
D000068698	MESH_DESCRIPTOR_UI
464205	PUBCHEM_CID
10948	IUPHAR_LIGAND_ID
99YXE507IL	UNII
117466	RXNORM
d04774	MMSL
009357	NDDF
395264002	SNOMEDCT_US
422091007	SNOMEDCT_US
206184-49-8	SECONDARY_CAS_RN
99YXE507IL	INXIGHT DRUGS

Pharmaceutical products:

None

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tenofovir 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Description:

Drug dosage:

ADMET properties:

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Approvals:

FDA Adverse Event Reporting System (Female)

FDA Adverse Event Reporting System (Male)

FDA Adverse Event Reporting System (Geriatric)

FDA Adverse Event Reporting System (Pediatric)

Pharmacologic Action:

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

🐶 Veterinary Drug Use

🐶 Veterinary products

Acid dissociation constants calculated using MoKa v3.0.0

Orange Book patent data (new drug applications)

Orange Book exclusivity data (new drug applications)

Bioactivity Summary:

External reference:

Pharmaceutical products: