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
May 27, 2023	EMA	ROCHE REGISTRATION GMBH
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	544.48	90.84	110	2828	6220	63479864
Jaundice cholestatic	528.48	90.84	110	2828	7214	63478870
Schizophrenia	505.92	90.84	112	2826	9840	63476244
Psychotic disorder	395.73	90.84	111	2827	25601	63460483
Hepatotoxicity	368.38	90.84	114	2824	36927	63449157
Blood bilirubin increased	355.42	90.84	111	2827	37029	63449055
Cholelithiasis	337.10	90.84	111	2827	43814	63442270
Asthma-chronic obstructive pulmonary disease overlap syndrome	189.87	90.84	38	2900	2023	63484061
Total lung capacity increased	185.54	90.84	38	2900	2272	63483812
Hepatic enzyme increased	174.63	90.84	111	2827	202217	63283867
Nasal polyps	149.20	90.84	38	2900	6001	63480083
Sarcoidosis	142.98	90.84	38	2900	7084	63479000
Rhinitis allergic	124.24	90.84	38	2900	11689	63474395
Bronchiectasis	116.25	90.84	39	2899	16103	63469981
Cardiac murmur	116.17	90.84	38	2900	14514	63471570
Vomiting	112.51	90.84	133	2805	559484	62926600
Viral mutation identified	111.97	90.84	24	2914	1786	63484298
Condition aggravated	110.96	90.84	113	2825	402104	63083980
Pneumonia	104.19	90.84	116	2822	456651	63029433
Lipodystrophy acquired	99.78	90.84	21	2917	1431	63484653

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	1027.21	31.47	439	5585	96659	34854248
Drug interaction	719.83	31.47	456	5568	225490	34725417
Mitochondrial toxicity	621.16	31.47	133	5891	2566	34948341
Lipodystrophy acquired	598.24	31.47	134	5890	3210	34947697
Eyelid ptosis	510.89	31.47	131	5893	5635	34945272
Psychiatric decompensation	445.90	31.47	103	5921	2834	34948073
Depression suicidal	407.81	31.47	93	5931	2412	34948495
Tearfulness	396.69	31.47	92	5932	2575	34948332
Loss of personal independence in daily activities	377.42	31.47	159	5865	33020	34917887
Diplopia	360.88	31.47	128	5896	16715	34934192
Progressive external ophthalmoplegia	342.89	31.47	73	5951	1362	34949545
Depressive symptom	338.45	31.47	82	5942	2777	34948130
Psychomotor skills impaired	317.86	31.47	83	5941	3823	34947084
Paranoia	259.40	31.47	92	5932	11976	34938931
Psychotic disorder	218.48	31.47	99	5925	24353	34926554
Injection site reaction	205.00	31.47	79	5945	12954	34937953
Suicidal ideation	158.29	31.47	94	5930	40294	34910613
Psychomotor retardation	126.86	31.47	40	5984	3610	34947297
Anxiety	116.16	31.47	112	5912	99316	34851591
Ophthalmoplegia	111.46	31.47	31	5993	1809	34949098
Prescribed overdose	88.34	31.47	41	5983	10606	34940301
Acquired immunodeficiency syndrome	82.97	31.47	19	6005	499	34950408
Immune reconstitution inflammatory syndrome	76.63	31.47	35	5989	8724	34942183
Virologic failure	68.90	31.47	25	5999	3455	34947452
Dysphagia	54.12	31.47	60	5964	62321	34888586
Injection site nodule	52.52	31.47	17	6007	1666	34949241
HIV infection	47.87	31.47	15	6009	1324	34949583
Incorrect route of product administration	41.61	31.47	28	5996	14817	34936090
Kaposi's sarcoma	40.58	31.47	12	6012	871	34950036
Dyschromatopsia	39.58	31.47	10	6014	401	34950506
HIV wasting syndrome	35.50	31.47	7	6017	87	34950820
End stage AIDS	34.78	31.47	6	6018	33	34950874
Intentional product use issue	34.73	31.47	47	5977	59769	34891138

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	905.79	44.63	425	6924	216365	79520674
Drug interaction	706.72	44.63	449	6900	414734	79322305
Mitochondrial toxicity	672.64	44.63	131	7218	2983	79734056
Lipodystrophy acquired	664.73	44.63	137	7212	4188	79732851
Psychotic disorder	618.31	44.63	205	7144	41197	79695842
Eyelid ptosis	512.40	44.63	132	7217	10912	79726127
Psychiatric decompensation	473.56	44.63	102	7247	3861	79733178
Hypomania	448.55	44.63	110	7239	7434	79729605
Depression suicidal	420.45	44.63	92	7257	3750	79733289
Jaundice cholestatic	404.60	44.63	110	7239	11174	79725865
Progressive external ophthalmoplegia	387.88	44.63	73	7276	1372	79735667
Schizophrenia	374.85	44.63	111	7238	15329	79721710
Tearfulness	373.84	44.63	91	7258	5954	79731085
Diplopia	349.31	44.63	127	7222	33339	79703700
Psychomotor skills impaired	340.03	44.63	82	7267	5155	79731884
Depressive symptom	318.46	44.63	81	7268	6342	79730697
Loss of personal independence in daily activities	281.03	44.63	152	7197	102428	79634611
Paranoia	268.80	44.63	91	7258	19341	79717698
Hepatotoxicity	267.13	44.63	118	7231	51234	79685805
Cholelithiasis	242.04	44.63	111	7238	52553	79684486
Blood bilirubin increased	232.51	44.63	116	7233	66116	79670923
Hepatic enzyme increased	161.79	44.63	134	7215	182476	79554563
Total lung capacity increased	159.52	44.63	38	7311	2260	79734779
Suicidal ideation	152.05	44.63	92	7257	76248	79660791
Asthma-chronic obstructive pulmonary disease overlap syndrome	146.78	44.63	38	7311	3183	79733856
Psychomotor retardation	122.26	44.63	38	7311	6146	79730893
Nasal polyps	115.92	44.63	38	7311	7289	79729750
Sarcoidosis	115.04	44.63	39	7310	8296	79728743
Ophthalmoplegia	111.83	44.63	30	7319	2882	79734157
Injection site reaction	103.83	44.63	64	7285	54721	79682318
Rhinitis allergic	96.79	44.63	38	7311	12231	79724808
Virologic failure	96.68	44.63	29	7320	4162	79732877
Viral mutation identified	94.66	44.63	28	7321	3830	79733209
Cardiac murmur	90.72	44.63	39	7310	15785	79721254
Anxiety	89.22	44.63	112	7237	248400	79488639
Immune reconstitution inflammatory syndrome	85.60	44.63	36	7313	13805	79723234
Bronchiectasis	74.86	44.63	38	7311	22348	79714691
Prescribed overdose	63.58	44.63	41	7308	37842	79699197
Pathogen resistance	58.86	44.63	28	7321	14314	79722725
Lung neoplasm malignant	56.55	44.63	34	7315	27758	79709281
Dysphagia	55.22	44.63	62	7287	122074	79614965
Multiple-drug resistance	51.43	44.63	22	7327	8786	79728253

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