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

Stem definition	Drug id	CAS RN
peptides and glycopeptides	1010	159519-65-0

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: enfuvirtide fuzeon pentafuside	Enfuvirtide interferes with the entry of HIV-1 into cells by inhibiting fusion of viral and cellular membranes. Enfuvirtide binds to the first heptad-repeat (HR1) in the gp41 subunit of the viral envelope glycoprotein and prevents the conformational changes required for the fusion of viral and cellular membranes. Molecular weight: 4491.95 Formula: C204H301N51O64 CLOGP: LIPINSKI: None HAC: 115 HDO: 63 TPSA: 1902.89 ALOGS: ROTB: 151

Molecule

Description

Molfile Inchi Smiles

Synonyms:

enfuvirtide
fuzeon
pentafuside

Enfuvirtide interferes with the entry of HIV-1 into cells by inhibiting fusion of viral and cellular membranes. Enfuvirtide binds to the first heptad-repeat (HR1) in the gp41 subunit of the viral envelope glycoprotein and prevents the conformational changes required for the fusion of viral and cellular membranes.

Molecular weight: 4491.95
Formula: C204H301N51O64
CLOGP:
LIPINSKI: None
HAC: 115
HDO: 63
TPSA: 1902.89
ALOGS:
ROTB: 151

Drug dosage:

Dose	Unit	Route
0.18	g	P

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	1000 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)	0.57 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	0.07 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	0.36 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.08 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	4 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
March 13, 2003	FDA	ROCHE

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
Hypomania	373.09	76.54	74	1988	4828	56285177
Jaundice cholestatic	364.34	76.54	74	1988	5445	56284560
Schizophrenia	322.23	76.54	75	1987	10424	56279581
Psychotic disorder	257.59	76.54	74	1988	23484	56266521
Hepatotoxicity	254.12	76.54	78	1984	31075	56258930
Blood bilirubin increased	236.35	76.54	75	1987	33279	56256726
Cholelithiasis	219.97	76.54	74	1988	39390	56250615
Hepatic enzyme increased	118.47	76.54	75	1987	171309	56118696
Viral mutation identified	95.44	76.54	20	2042	1694	56288311
Vomiting	83.12	76.54	96	1966	498132	55791873

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
Depression	912.11	29.46	395	5030	90420	31601499
Mitochondrial toxicity	622.84	29.46	132	5293	2441	31689478
Drug interaction	617.39	29.46	401	5024	208142	31483777
Lipodystrophy acquired	597.05	29.46	133	5292	3131	31688788
Eyelid ptosis	514.19	29.46	130	5295	5325	31686594
Diplopia	379.64	29.46	127	5298	14035	31677884
Loss of personal independence in daily activities	334.17	29.46	139	5286	28149	31663770
Progressive external ophthalmoplegia	334.10	29.46	71	5354	1323	31690596
Psychiatric decompensation	241.03	29.46	58	5367	1918	31690001
Depression suicidal	230.56	29.46	54	5371	1586	31690333
Injection site reaction	214.21	29.46	79	5346	11572	31680347
Tearfulness	211.72	29.46	52	5373	1875	31690044
Depressive symptom	158.20	29.46	42	5383	2072	31689847
Psychomotor skills impaired	141.93	29.46	42	5383	3085	31688834
Paranoia	131.53	29.46	54	5371	10501	31681418
Ophthalmoplegia	112.90	29.46	31	5394	1737	31690182
Psychotic disorder	106.67	29.46	59	5366	22234	31669685
HIV infection	96.97	29.46	27	5398	1593	31690326
Acquired immunodeficiency syndrome	83.66	29.46	19	5406	484	31691435
Immune reconstitution inflammatory syndrome	75.96	29.46	34	5391	8144	31683775
Suicidal ideation	71.23	29.46	55	5370	36351	31655568
Virologic failure	67.58	29.46	24	5401	3141	31688778
Psychomotor retardation	66.94	29.46	24	5401	3228	31688691
Dysphagia	58.39	29.46	60	5365	57616	31634303
Anxiety	57.19	29.46	74	5351	90959	31600960
Injection site nodule	54.41	29.46	17	5408	1497	31690422
Prescribed overdose	54.25	29.46	28	5397	9164	31682755
Dyschromatopsia	41.59	29.46	10	5415	328	31691591
Kaposi's sarcoma	40.67	29.46	12	5413	870	31691049
HIV wasting syndrome	35.62	29.46	7	5418	86	31691833
End stage AIDS	34.97	29.46	6	5419	32	31691887
Injection site pain	34.95	29.46	36	5389	34598	31657321
Blood lactic acid increased	31.42	29.46	17	5408	6113	31685806
Injection site induration	31.11	29.46	13	5412	2634	31689285

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
Depression	844.20	39.87	382	5534	198592	70723936
Mitochondrial toxicity	688.52	39.87	130	5786	2780	70919748
Lipodystrophy acquired	676.18	39.87	136	5780	4080	70918448
Drug interaction	643.24	39.87	395	5521	381046	70541482
Eyelid ptosis	532.37	39.87	131	5785	9971	70912557
Progressive external ophthalmoplegia	384.47	39.87	71	5845	1333	70921195
Diplopia	379.49	39.87	126	5790	28021	70894507
Psychotic disorder	358.36	39.87	130	5786	37571	70884957
Hypomania	295.81	39.87	74	5842	5998	70916530
Jaundice cholestatic	265.45	39.87	74	5842	9110	70913418
Loss of personal independence in daily activities	262.54	39.87	132	5784	84778	70837750
Psychiatric decompensation	253.19	39.87	57	5859	2930	70919598
Depression suicidal	233.36	39.87	53	5863	2834	70919694
Schizophrenia	221.52	39.87	74	5842	16694	70905834
Tearfulness	194.56	39.87	51	5865	4969	70917559
Hepatotoxicity	176.95	39.87	82	5834	43904	70878624
Psychomotor skills impaired	153.95	39.87	41	5875	4243	70918285
Blood bilirubin increased	147.34	39.87	80	5836	59821	70862707
Cholelithiasis	147.24	39.87	74	5842	47266	70875262
Depressive symptom	146.23	39.87	41	5875	5140	70917388
Paranoia	139.70	39.87	53	5863	17235	70905293
Ophthalmoplegia	115.82	39.87	30	5886	2785	70919743
Injection site reaction	115.43	39.87	64	5852	49788	70872740
Hepatic enzyme increased	112.96	39.87	98	5818	156892	70765636
Immune reconstitution inflammatory syndrome	87.81	39.87	35	5881	12955	70909573
Virologic failure	84.24	39.87	25	5891	3825	70918703
Viral mutation identified	81.35	39.87	24	5892	3598	70918930
Suicidal ideation	70.21	39.87	53	5863	69543	70852985
Psychomotor retardation	67.14	39.87	23	5893	5575	70916953
Dysphagia	64.53	39.87	62	5854	112772	70809756
Multiple-drug resistance	57.41	39.87	22	5894	7333	70915195
HIV infection	52.98	39.87	14	5902	1403	70921125
Pathogen resistance	50.97	39.87	24	5892	13255	70909273
Anxiety	47.72	39.87	74	5842	220256	70702272
Prescribed overdose	44.71	39.87	28	5888	27153	70895375
Dyschromatopsia	40.91	39.87	10	5906	733	70921795

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	J05AX07	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Other antivirals
MeSH PA	D019380	Anti-HIV Agents
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D044966	Anti-Retroviral Agents
MeSH PA	D000998	Antiviral Agents
MeSH PA	D023581	HIV Fusion Inhibitors
FDA MoA	N0000175615	Fusion Protein Inhibitors
FDA EPC	N0000175616	Human Immunodeficiency Virus 1 Fusion Inhibitor
CHEBI has role	CHEBI:59886	HIV fusion 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
Pneumonia	contraindication	233604007	DOID:552
Breastfeeding (mother)	contraindication	413712001
Smokes tobacco daily	contraindication	449868002

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	3.09	acidic
pKa2	3.55	acidic
pKa3	3.77	acidic
pKa4	3.97	acidic
pKa5	4.16	acidic
pKa6	4.38	acidic
pKa7	4.66	acidic
pKa8	9.65	acidic
pKa9	11.84	acidic
pKa10	12.17	acidic
pKa11	12.25	acidic
pKa12	12.34	acidic
pKa13	12.44	acidic
pKa14	12.6	acidic
pKa15	12.67	acidic
pKa16	12.74	acidic
pKa17	12.82	acidic
pKa18	12.92	acidic
pKa19	12.93	acidic
pKa20	13.14	acidic
pKa21	13.18	acidic
pKa22	13.22	acidic
pKa23	13.23	acidic
pKa24	13.3	acidic
pKa25	13.43	acidic
pKa26	13.44	acidic
pKa27	13.49	acidic
pKa28	13.53	acidic
pKa29	13.57	acidic
pKa30	13.59	acidic
pKa31	13.65	acidic
pKa32	13.78	acidic
pKa33	13.78	acidic
pKa34	13.8	acidic
pKa35	13.88	acidic
pKa36	13.93	acidic
pKa37	11.11	Basic
pKa38	10.51	Basic
pKa39	6.69	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Transmembrane glycoprotein gp41	Membrane other	O40239_9PLVG	INHIBITOR			CHEMBL	CHEMBL
Envelope glycoprotein	Viral envelope protein	Q53I07_9HIV1				WOMBAT-PK
GP41	Unclassified	Q76270_9HIV1		EC50	8	CHEMBL

External reference:

ID	Source
4021375	VUID
N0000171600	NUI
D02499	KEGG_DRUG
4021375	VANDF
C0537439	UMLSCUI
CHEBI:608828	CHEBI
CHEMBL525076	ChEMBL_ID
D000077560	MESH_DESCRIPTOR_UI
DB00109	DRUGBANK_ID
8063	INN_ID
19OWO1T3ZE	UNII
16130199	PUBCHEM_CID
139896	RXNORM
17175	MMSL
46376	MMSL
d04853	MMSL
009919	NDDF
398902008	SNOMEDCT_US
409127007	SNOMEDCT_US

Pharmaceutical products:

None