Search type

Query format

Minimum Tanimoto similarity

Fingerprint

Tox | Related Drugs | BioActivity |

Stem definition	Drug id	CAS RN
N-methylated xanthine derivatives	2099	6493-05-6

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: pentoxifylline azupentat dimethyloxohexylxanthine oxpentifylline pentoxifyllin	A METHYLXANTHINE derivative that inhibits phosphodiesterase and affects blood rheology. It improves blood flow by increasing erythrocyte and leukocyte flexibility. It also inhibits platelet aggregation. Pentoxifylline modulates immunologic activity by stimulating cytokine production. Molecular weight: 278.31 Formula: C13H18N4O3 CLOGP: 0.12 LIPINSKI: 0 HAC: 7 HDO: 0 TPSA: 75.51 ALOGS: -1.73 ROTB: 5 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

pentoxifylline
azupentat
dimethyloxohexylxanthine
oxpentifylline
pentoxifyllin

A METHYLXANTHINE derivative that inhibits phosphodiesterase and affects blood rheology. It improves blood flow by increasing erythrocyte and leukocyte flexibility. It also inhibits platelet aggregation. Pentoxifylline modulates immunologic activity by stimulating cytokine production.

Molecular weight: 278.31
Formula: C13H18N4O3
CLOGP: 0.12
LIPINSKI: 0
HAC: 7
HDO: 0
TPSA: 75.51
ALOGS: -1.73
ROTB: 5

Status: OFP

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

Drug dosage:

Dose	Unit	Route
1	g	O
0.30	g	P

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	191 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	0 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	71.86 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	25 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	1.80 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	39 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.51 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	1.20 hours	Lombardo F, Berellini G, Obach RS

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Property	Description	Value	Unit	Confidence	Similarity
pfas-class	PFAS structural alert (1 = True, 0 = False)	0

Approvals:

Date	Agency	Company	Orphan
Aug. 30, 1984	FDA

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
Body tinea	210.42	18.95	45	6507	2103	90619792
Inhibitory drug interaction	187.80	18.95	44	6508	3119	90618776
Infection susceptibility increased	183.41	18.95	45	6507	3881	90618014
Poor quality sleep	156.47	18.95	61	6491	24632	90597263
Glucose tolerance impaired	151.75	18.95	45	6507	7940	90613955
Purpura	135.88	18.95	48	6504	14730	90607165
Impaired quality of life	128.57	18.95	52	6500	23092	90598803
Impaired work ability	126.88	18.95	49	6503	19277	90602618
Bone density decreased	117.52	18.95	45	6507	17300	90604595
Hyperlipidaemia	108.70	18.95	46	6506	22870	90599025
Oral herpes	89.03	18.95	45	6507	33479	90588416
Skin disorder	88.02	18.95	46	6506	36660	90585235
Femoral neck fracture	81.88	18.95	30	6522	10203	90611692
Cataract	80.00	18.95	55	6497	72037	90549858
Cellulitis	79.23	18.95	60	6492	91277	90530618
Herpes zoster	66.65	18.95	55	6497	94589	90527306
International normalised ratio increased	47.57	18.95	34	6518	47282	90574613
Insomnia	43.99	18.95	83	6469	333391	90288504
Ischaemic stroke	42.60	18.95	24	6528	22142	90599753
Drug ineffective for unapproved indication	37.32	18.95	34	6518	66610	90555285
Drug ineffective	35.18	18.95	194	6358	1384104	89237791
Drug interaction	31.80	18.95	65	6487	276388	90345507
Peripheral ischaemia	25.61	18.95	11	6541	5656	90616239
Deafness bilateral	25.47	18.95	8	6544	1705	90620190
Stevens-Johnson syndrome	24.78	18.95	19	6533	29357	90592538
Insulin resistance	24.07	18.95	7	6545	1151	90620744
Prerenal failure	23.82	18.95	8	6544	2107	90619788
Skin ulcer	23.18	18.95	23	6529	50052	90571843
Pseudomonas infection	23.03	18.95	14	6538	14851	90607044
Renal failure	22.95	18.95	37	6515	130970	90490925
Contusion	22.02	18.95	53	6499	251163	90370732
Melaena	21.95	18.95	19	6533	34778	90587117
Allodynia	20.45	18.95	6	6546	1018	90620877
Hypertension	20.44	18.95	76	6476	457456	90164439
Infusion related reaction	20.27	18.95	3	6549	416777	90205118
Osteonecrosis	20.03	18.95	16	6536	26225	90595670
Clostridium test positive	19.64	18.95	9	6543	5392	90616503

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
Sedation complication	57.21	18.50	19	5109	2900	42613307
Akathisia	54.07	18.50	26	5102	10425	42605782
Arrhythmia	41.10	18.50	36	5092	40281	42575926
Peripheral artery occlusion	40.28	18.50	13	5115	1813	42614394
Blood lactic acid	39.44	18.50	9	5119	337	42615870
Hyperkalaemia	38.68	18.50	48	5080	80410	42535797
Pleural mass	38.39	18.50	7	5121	82	42616125
Acute kidney injury	36.80	18.50	112	5016	367225	42248982
Biopsy lymph gland	33.42	18.50	6	5122	64	42616143
Peripheral ischaemia	33.14	18.50	16	5112	6469	42609738
Skin hyperpigmentation	33.09	18.50	14	5114	4167	42612040
Heart valve stenosis	32.70	18.50	6	5122	73	42616134
Mitral valve prolapse	28.55	18.50	8	5120	689	42615518
Radiotherapy to brain	27.88	18.50	5	5123	53	42616154
Drug dependence	27.70	18.50	25	5103	29069	42587138
Aortic bruit	26.05	18.50	6	5122	234	42615973
Intentional product misuse	25.15	18.50	34	5094	61866	42554341
Myocardial necrosis	25.05	18.50	6	5122	278	42615929
Basal cell carcinoma	24.57	18.50	21	5107	22712	42593495
Agitation	24.13	18.50	34	5094	64280	42551927
Endarterectomy	22.58	18.50	5	5123	163	42616044
Penile pain	21.15	18.50	8	5120	1780	42614427
Oesophageal dilatation	20.50	18.50	5	5123	250	42615957
International normalised ratio increased	20.39	18.50	27	5101	48141	42568066
Metabolic syndrome	20.34	18.50	8	5120	1975	42614232
Hilar lymphadenopathy	20.06	18.50	7	5121	1239	42614968
Ventricular enlargement	19.83	18.50	6	5122	677	42615530
Atrial enlargement	19.44	18.50	6	5122	723	42615484
Paraesthesia	19.37	18.50	33	5095	73426	42542781
Extremity necrosis	19.13	18.50	8	5120	2311	42613896
Skin squamous cell carcinoma recurrent	18.65	18.50	4	5124	112	42616095

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
Body tinea	189.60	15.14	44	11415	2071	110575769
Infection susceptibility increased	157.62	15.14	44	11415	4354	110573486
Glucose tolerance impaired	149.68	15.14	51	11408	9786	110568054
Inhibitory drug interaction	148.06	15.14	43	11416	4904	110572936
Poor quality sleep	118.61	15.14	58	11401	28019	110549821
Purpura	107.89	15.14	52	11407	24336	110553504
Bone density decreased	101.89	15.14	44	11415	15998	110561842
Impaired work ability	92.31	15.14	48	11411	26371	110551469
Impaired quality of life	92.07	15.14	50	11409	29967	110547873
Hyperlipidaemia	73.55	15.14	46	11413	35802	110542038
Femoral neck fracture	68.61	15.14	31	11428	12536	110565304
Oral herpes	68.29	15.14	44	11415	36036	110541804
Skin disorder	63.67	15.14	45	11414	42868	110534972
Cataract	59.68	15.14	56	11403	79429	110498411
Peripheral ischaemia	59.49	15.14	27	11432	11031	110566809
Amaurosis fugax	59.41	15.14	18	11441	2372	110575468
International normalised ratio increased	57.36	15.14	57	11402	86715	110491125
Hyperkalaemia	48.65	15.14	65	11394	135731	110442109
Cellulitis	47.74	15.14	62	11397	125954	110451886
Akathisia	45.62	15.14	26	11433	17087	110560753
Herpes zoster	43.70	15.14	55	11404	108324	110469516
Urinary tract disorder	43.68	15.14	18	11441	5826	110572014
Acute kidney injury	43.04	15.14	154	11305	635276	109942564
Drug ineffective for unapproved indication	39.58	15.14	51	11408	102787	110475053
Pleural mass	38.02	15.14	7	11452	102	110577738
Blood lactic acid	37.88	15.14	9	11450	469	110577371
Arrhythmia	37.53	15.14	41	11418	69534	110508306
Peripheral artery occlusion	36.26	15.14	13	11446	2892	110574948
Drug interaction	35.35	15.14	123	11336	500060	110077780
Drug ineffective	35.21	15.14	273	11186	1520267	109057573
Haemorrhagic stroke	34.22	15.14	20	11439	13769	110564071
Peripheral vascular disorder	34.07	15.14	17	11442	8559	110569281
Biopsy lymph gland	31.50	15.14	6	11453	106	110577734
Ocular discomfort	31.23	15.14	16	11443	8517	110569323
Skin hyperpigmentation	30.94	15.14	16	11443	8680	110569160
Insomnia	30.23	15.14	94	11365	360496	110217344
Joint swelling	29.88	15.14	5	11454	442840	110135000
Drug dependence	29.66	15.14	31	11428	49989	110527851
Extremity necrosis	29.40	15.14	12	11447	3790	110574050
Radiotherapy to brain	29.08	15.14	5	11454	48	110577792
Ischaemic stroke	28.92	15.14	28	11431	41235	110536605
Heart valve stenosis	28.50	15.14	6	11453	179	110577661
Skin ulcer	26.76	15.14	33	11426	63612	110514228
Aortic bruit	26.24	15.14	6	11453	264	110577576
Peripheral coldness	24.21	15.14	18	11441	18522	110559318
Haematuria	24.17	15.14	36	11423	82969	110494871
Sedation complication	23.11	15.14	18	11441	19837	110558003
Myocardial necrosis	21.95	15.14	6	11453	549	110577291
Telangiectasia	21.93	15.14	8	11451	1869	110575971
Generalised oedema	21.83	15.14	21	11438	30683	110547157
Melaena	21.73	15.14	31	11428	68726	110509114
Head discomfort	21.63	15.14	17	11442	18983	110558857
Systemic scleroderma	21.55	15.14	8	11451	1964	110575876
Penile pain	21.43	15.14	7	11452	1177	110576663
Ventricular enlargement	20.37	15.14	6	11453	718	110577122
Mitral valve prolapse	20.09	15.14	8	11451	2370	110575470
Presyncope	19.99	15.14	25	11434	48862	110528978
Arthropathy	19.94	15.14	3	11456	287519	110290321
Intermittent claudication	19.79	15.14	9	11450	3692	110574148
Anaemia	19.73	15.14	110	11349	546976	110030864
Skin squamous cell carcinoma recurrent	19.31	15.14	4	11455	110	110577730
Deafness bilateral	19.10	15.14	8	11451	2696	110575144
Hypersensitivity	19.07	15.14	9	11450	403989	110173851
Endarterectomy	18.99	15.14	5	11454	396	110577444
Cardio-respiratory arrest	18.99	15.14	39	11420	115797	110462043
Rheumatoid arthritis	18.88	15.14	4	11455	299609	110278231
Insulin resistance	18.82	15.14	7	11452	1727	110576113
Synovitis	18.69	15.14	3	11456	274089	110303751
Coma	18.53	15.14	39	11420	117830	110460010
Agitation	18.46	15.14	38	11421	113013	110464827
Haematoma	17.95	15.14	26	11433	58450	110519390
Hepatocellular injury	17.75	15.14	24	11435	50618	110527222
Fall	17.72	15.14	115	11344	603367	109974473
Metabolic syndrome	17.69	15.14	8	11451	3239	110574601
Atrial enlargement	17.63	15.14	6	11453	1145	110576695
Infusion related reaction	17.23	15.14	9	11450	381153	110196687
Contusion	16.98	15.14	58	11401	233303	110344537
Hilar lymphadenopathy	16.90	15.14	7	11452	2295	110575545
Oesophageal dilatation	16.86	15.14	5	11454	612	110577228
Systemic lupus erythematosus	16.86	15.14	3	11456	254335	110323505
Altered state of consciousness	16.79	15.14	25	11434	57601	110520239
Dihydrotestosterone increased	16.41	15.14	3	11456	42	110577798
Haematemesis	16.30	15.14	25	11434	59083	110518757
Drug hypersensitivity	16.13	15.14	14	11445	454076	110123764
Suspected product contamination	15.78	15.14	4	11455	273	110577567
Cardiac failure	15.78	15.14	49	11410	187577	110390263
Penile swelling	15.55	15.14	5	11454	801	110577039
Anticoagulation drug level decreased	15.54	15.14	4	11455	290	110577550
Nasopharyngitis	15.47	15.14	11	11448	394350	110183490
Intentional product misuse	15.40	15.14	39	11420	132865	110444975
Renal failure	15.34	15.14	55	11404	226519	110351321
Mycobacterium abscessus infection	15.33	15.14	6	11453	1700	110576140
Prerenal failure	15.28	15.14	8	11451	4451	110573389

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	C04AD03	CARDIOVASCULAR SYSTEM PERIPHERAL VASODILATORS PERIPHERAL VASODILATORS Purine derivatives
FDA PE	N0000009065	Hematologic Activity Alteration
MeSH PA	D000975	Antioxidants
MeSH PA	D002317	Cardiovascular Agents
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D006401	Hematologic Agents
MeSH PA	D010726	Phosphodiesterase Inhibitors
MeSH PA	D010975	Platelet Aggregation Inhibitors
MeSH PA	D011837	Radiation-Protective Agents
MeSH PA	D014665	Vasodilator Agents
MeSH PA	D016166	Free Radical Scavengers
MeSH PA	D020011	Protective Agents
FDA EPC	N0000175895	Blood Viscosity Reducer
CHEBI has role	CHEBI:22587	antiviral agent
CHEBI has role	CHEBI:35469	antidepressant
CHEBI has role	CHEBI:35476	antipsychotic agent
CHEBI has role	CHEBI:35526	hypoglycemic agent
CHEBI has role	CHEBI:35554	cardiovascular drug
CHEBI has role	CHEBI:35610	antineoplastic agent
CHEBI has role	CHEBI:35623	anticonvulsant
CHEBI has role	CHEBI:38068	antimalarial
CHEBI has role	CHEBI:48407	antiparkinson drug
CHEBI has role	CHEBI:62868	hepatoprotective agent
CHEBI has role	CHEBI:64946	anti-HIV agent
CHEBI has role	CHEBI:67079	anti-inflammatory agent
CHEBI has role	CHEBI:70868	antileishmanial agent
CHEBI has role	CHEBI:73336	vulnerary
CHEBI has role	CHEBI:75835	anti-anaemic agent
CHEBI has role	CHEBI:149553	anticoronaviral agent
CHEBI has role	CHEBI:231911	renoprotective agent
CHEBI has role	CHEBI:233423	antifibrotic agent

Related Drugs by ATC class:

C04AD Purine derivatives 3 drugs

etofylline nicotinate pentifylline xantinol

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

Disease	Relation	SNOMED_ID	DOID
Peripheral vascular disease	indication	400047006
Osteoradionecrosis	off-label use	109333005
Alcoholic hepatitis	off-label use	235875008
Retinal hemorrhage	contraindication	28998008
Blood coagulation disorder	contraindication	64779008	DOID:1247
Kidney disease	contraindication	90708001	DOID:557
Bleeding	contraindication	131148009
Hemorrhagic cerebral infarction	contraindication	230706003

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	1.43	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
Adenosine receptor A2b	GPCR	P29275	AA2BR_HUMAN	ANTAGONIST	Ki	5.29	CHEMBL	CHEMBL
cAMP-specific 3',5'-cyclic phosphodiesterase 4B	Enzyme	Q07343	PDE4B_HUMAN	INHIBITOR			WOMBAT-PK	CHEMBL
cGMP-specific 3',5'-cyclic phosphodiesterase	Enzyme	O76074	PDE5A_HUMAN	INHIBITOR			DRUGBANK	CHEMBL
Acetylcholinesterase	Enzyme	P22303	ACES_HUMAN		IC50	5.18	CHEMBL

External reference:

ID	Source
4018468	VUID
N0000146791	NUI
D00501	KEGG_DRUG
4018468	VANDF
C0030899	UMLSCUI
CHEBI:7986	CHEBI
PNX	PDB_CHEM_ID
CHEMBL628	ChEMBL_ID
DB00806	DRUGBANK_ID
D010431	MESH_DESCRIPTOR_UI
4740	PUBCHEM_CID
7095	IUPHAR_LIGAND_ID
3309	INN_ID
SD6QCT3TSU	UNII
8013	RXNORM
10203	MMSL
41909	MMSL
5257	MMSL
d00336	MMSL
002098	NDDF
387522004	SNOMEDCT_US
91376007	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Pentoxifylline	HUMAN PRESCRIPTION DRUG LABEL	1	0615-8511	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	17 sections
PENTOXIFYLLINE	HUMAN PRESCRIPTION DRUG LABEL	1	0904-5448	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	17 sections
Pentoxifylline	HUMAN PRESCRIPTION DRUG LABEL	1	16571-856	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	17 sections
PENTOXIFYLLINE	HUMAN PRESCRIPTION DRUG LABEL	1	16590-856	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	19 sections
PENTOXIFYLLINE	HUMAN PRESCRIPTION DRUG LABEL	1	33261-992	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	17 sections
Pentoxifylline	HUMAN PRESCRIPTION DRUG LABEL	1	43353-123	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	19 sections
Pentoxifylline	HUMAN PRESCRIPTION DRUG LABEL	1	53808-0516	TABLET, FILM COATED, EXTENDED RELEASE	400 mg	ORAL	ANDA	19 sections
Pentoxifylline	HUMAN PRESCRIPTION DRUG LABEL	1	53808-0757	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	19 sections
Pentoxifylline	HUMAN PRESCRIPTION DRUG LABEL	1	53808-0758	TABLET, FILM COATED, EXTENDED RELEASE	400 mg	ORAL	ANDA	19 sections
Pentoxifylline	HUMAN PRESCRIPTION DRUG LABEL	1	54868-4515	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	19 sections
PENTOXIFYLLINE	HUMAN PRESCRIPTION DRUG LABEL	1	60505-0033	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	17 sections
PENTOXIFYLLINE	HUMAN PRESCRIPTION DRUG LABEL	1	63629-2910	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	16 sections
PENTOXIFYLLINE	HUMAN PRESCRIPTION DRUG LABEL	1	67544-252	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	16 sections
Pentoxifylline	HUMAN PRESCRIPTION DRUG LABEL	1	68071-4532	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	19 sections
Pentoxifylline	HUMAN PRESCRIPTION DRUG LABEL	1	70954-668	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	17 sections
Pentoxifylline	HUMAN PRESCRIPTION DRUG LABEL	1	70954-668	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	17 sections
Pentoxifylline	HUMAN PRESCRIPTION DRUG LABEL	1	71335-2586	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	17 sections
PENTOXIFYLLINE	HUMAN PRESCRIPTION DRUG LABEL	1	72162-2113	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	16 sections
PENTOXIFYLLINE	HUMAN PRESCRIPTION DRUG LABEL	1	72189-025	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	9 sections
PENTOXIFYLLINE	HUMAN PRESCRIPTION DRUG LABEL	1	72189-025	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	9 sections
PENTOXIFYLLINE	HUMAN PRESCRIPTION DRUG LABEL	1	72189-025	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	9 sections
PENTOXIFYLLINE 0.5% / TRIAMCINOLONE ACETONIDE 0.1%	HUMAN PRESCRIPTION DRUG LABEL	2	72934-1169	GEL	0.50 g	TOPICAL	unapproved drug other	4 sections
BETAMETHASONE DIPROPIONATE 0.05% / MINOXIDIL 5% / NIACINAMIDE 2% / PENTOXIFYLLINE 0.5%	HUMAN PRESCRIPTION DRUG LABEL	4	72934-4024	SOLUTION	2 g	TOPICAL	unapproved drug other	4 sections