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

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	144.05	18.10	32	4984	1295	50598813
Infection susceptibility increased	122.85	18.10	32	4984	2552	50597556
Inhibitory drug interaction	122.52	18.10	31	4985	2202	50597906
Glucose tolerance impaired	101.23	18.10	32	4984	5086	50595022
Impaired quality of life	95.93	18.10	32	4984	6024	50594084
Purpura	91.16	18.10	35	4981	9876	50590232
Femoral neck fracture	78.11	18.10	29	4987	7461	50592647
Bone density decreased	77.11	18.10	32	4984	11043	50589065
Poor quality sleep	70.63	18.10	34	4982	16612	50583496
Hyperlipidaemia	66.06	18.10	33	4983	17457	50582651
Impaired work ability	64.42	18.10	30	4986	13610	50586498
Oral herpes	58.01	18.10	32	4984	20693	50579415
Skin disorder	53.60	18.10	32	4984	23998	50576110
Cellulitis	49.56	18.10	47	4969	70751	50529357
Cataract	42.17	18.10	36	4980	47264	50552844
Herpes zoster	36.75	18.10	40	4976	70746	50529362
International normalised ratio increased	34.75	18.10	31	4985	43121	50556987
Deafness bilateral	25.63	18.10	8	5008	1218	50598890
Peripheral ischaemia	25.25	18.10	11	5005	4265	50595843
Pseudomonas infection	24.84	18.10	14	5002	9416	50590692
Insomnia	24.83	18.10	54	4962	174811	50425297
Hypertension	24.26	18.10	60	4956	211143	50388965
Prerenal failure	24.08	18.10	8	5008	1485	50598623
Stevens-Johnson syndrome	22.38	18.10	18	4998	21734	50578374
Allodynia	20.90	18.10	6	5010	686	50599422
Drug interaction	20.12	18.10	54	4962	199567	50400541
Renal failure	20.00	18.10	37	4979	106596	50493512
Contusion	19.89	18.10	38	4978	112145	50487963
Necrotising myositis	19.48	18.10	5	5011	375	50599733
Corneal leukoma	19.46	18.10	3	5013	14	50600094
Melaena	19.08	18.10	18	4998	26846	50573262
Delirium	18.80	18.10	21	4995	38171	50561937
Drug ineffective for unapproved indication	18.55	18.10	16	5000	21265	50578843
Skin ulcer	18.38	18.10	20	4996	35298	50564810

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
Acute kidney injury	48.33	17.84	105	3672	265162	29305588
Pleural mass	39.46	17.84	7	3770	65	29570685
Blood lactic acid	38.90	17.84	9	3768	337	29570413
Hyperkalaemia	38.19	17.84	43	3734	61349	29509401
Peripheral artery occlusion	38.16	17.84	12	3765	1450	29569300
Skin hyperpigmentation	37.42	17.84	14	3763	2850	29567900
Drug dependence	33.58	17.84	25	3752	20956	29549794
Biopsy lymph gland	33.51	17.84	6	3771	59	29570691
Mitral valve prolapse	29.65	17.84	8	3769	564	29570186
Peripheral ischaemia	29.58	17.84	14	3763	5105	29565645
Radiotherapy to brain	28.85	17.84	5	3772	40	29570710
Paraesthesia	24.16	17.84	32	3745	53813	29516937
Endarterectomy	22.88	17.84	5	3772	144	29570606
Metabolic syndrome	22.20	17.84	8	3769	1465	29569285
Hilar lymphadenopathy	22.14	17.84	7	3770	860	29569890
Hypomagnesaemia	21.85	17.84	18	3759	17450	29553300
Extremity necrosis	21.54	17.84	8	3769	1595	29569155
International normalised ratio increased	20.88	17.84	27	3750	44345	29526405
Anaemia	19.43	17.84	63	3714	200888	29369862
Gingival disorder	19.33	17.84	7	3770	1299	29569451
Penile pain	18.74	17.84	7	3770	1417	29569333
Therapeutic response decreased	18.30	17.84	19	3758	24692	29546058

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	131.89	15.83	31	8106	1262	64489333
Glucose tolerance impaired	109.00	15.83	38	8099	6405	64484190
Infection susceptibility increased	108.94	15.83	31	8106	2695	64487900
Inhibitory drug interaction	96.00	15.83	30	8107	3597	64486998
Impaired quality of life	82.62	15.83	31	8106	6440	64484155
Purpura	75.82	15.83	39	8098	17207	64473388
Bone density decreased	69.71	15.83	31	8106	9921	64480674
Femoral neck fracture	67.02	15.83	29	8108	8695	64481900
Peripheral ischaemia	55.18	15.83	25	8112	8353	64482242
Impaired work ability	54.44	15.83	30	8107	15189	64475406
Poor quality sleep	53.46	15.83	32	8105	18919	64471676
Hyperlipidaemia	50.22	15.83	33	8104	22943	64467652
Acute kidney injury	49.33	15.83	146	7991	449094	64041501
International normalised ratio increased	47.24	15.83	54	8083	79113	64411482
Oral herpes	46.44	15.83	31	8106	22121	64468474
Hyperkalaemia	44.24	15.83	59	8078	101070	64389525
Skin disorder	40.23	15.83	31	8106	27649	64462946
Pleural mass	38.98	15.83	7	8130	71	64490524
Blood lactic acid	36.40	15.83	9	8128	454	64490141
Peripheral artery occlusion	33.82	15.83	12	8125	2126	64488469
Drug dependence	33.21	15.83	30	8107	33282	64457313
Cellulitis	32.60	15.83	49	8088	93608	64396987
Cataract	32.33	15.83	36	8101	51226	64439369
Skin hyperpigmentation	32.25	15.83	16	8121	6535	64484060
Biopsy lymph gland	30.88	15.83	6	8131	96	64490499
Peripheral vascular disorder	30.70	15.83	16	8121	7245	64483350
Radiotherapy to brain	28.69	15.83	5	8132	42	64490553
Extremity necrosis	27.44	15.83	11	8126	2723	64487872
Herpes zoster	26.94	15.83	41	8096	79146	64411449
Peripheral coldness	26.06	15.83	18	8119	13566	64477029
Deafness bilateral	20.41	15.83	8	8129	1868	64488727
Drug interaction	20.39	15.83	95	8042	361988	64128607
Mitral valve prolapse	20.20	15.83	8	8129	1919	64488676
Hypertension	19.23	15.83	74	8063	259187	64231408
Endarterectomy	19.03	15.83	5	8132	322	64490273
Anaemia	18.91	15.83	96	8041	378584	64112011
Haematoma	18.71	15.83	26	8111	46224	64444371
Metabolic syndrome	18.67	15.83	8	8129	2340	64488255
Melaena	18.60	15.83	28	8109	53520	64437075
Hilar lymphadenopathy	18.23	15.83	7	8130	1546	64489049
Penile pain	17.95	15.83	6	8131	889	64489706
Contusion	17.45	15.83	42	8095	113923	64376672
Mycobacterium abscessus infection	17.22	15.83	6	8131	1008	64489587
Skin ulcer	16.72	15.83	24	8113	43950	64446645
Hypomagnesaemia	16.62	15.83	22	8115	37354	64453241
Mucosa vesicle	16.57	15.83	3	8134	32	64490563
Prerenal failure	16.25	15.83	8	8129	3214	64487381
Hepatocellular injury	16.20	15.83	24	8113	45211	64445384
Chillblains	15.97	15.83	4	8133	213	64490382
Allodynia	15.84	15.83	6	8131	1277	64489318

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	D016166	Free Radical Scavengers
MeSH PA	D006401	Hematologic Agents
MeSH PA	D010726	Phosphodiesterase Inhibitors
MeSH PA	D010975	Platelet Aggregation Inhibitors
MeSH PA	D020011	Protective Agents
MeSH PA	D011837	Radiation-Protective Agents
MeSH PA	D014665	Vasodilator Agents
FDA EPC	N0000175895	Blood Viscosity Reducer

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	0615-8305	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	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	68682-101	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	20 sections
Pentoxifylline	HUMAN PRESCRIPTION DRUG LABEL	1	68682-101	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	20 sections
PENTOXIFYLLINE	HUMAN PRESCRIPTION DRUG LABEL	1	70518-1285	TABLET, EXTENDED RELEASE	400 mg	ORAL	ANDA	17 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