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

Stem definition	Drug id	CAS RN
vinca alkaloids	2827	71486-22-1

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: vinorelbin ditartrate noranhydrovinblastine tartrate vinorelbine navelbin navelbine base 5'-anhydrovinblastine vinorelbine tartrate vinorelbine ditartrate navelbine vinorelbine base	A vinca alkaloid related to VINBLASTINE that is used as a first-line treatment for NON-SMALL CELL LUNG CANCER, or for advanced or metastatic BREAST CANCER refractory to treatment with ANTHRACYCLINES. Molecular weight: 778.95 Formula: C45H54N4O8 CLOGP: 5.94 LIPINSKI: 3 HAC: 12 HDO: 2 TPSA: 133.87 ALOGS: -4.81 ROTB: 10 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

vinorelbin ditartrate
noranhydrovinblastine tartrate
vinorelbine
navelbin
navelbine base
5'-anhydrovinblastine
vinorelbine tartrate
vinorelbine ditartrate
navelbine
vinorelbine base

A vinca alkaloid related to VINBLASTINE that is used as a first-line treatment for NON-SMALL CELL LUNG CANCER, or for advanced or metastatic BREAST CANCER refractory to treatment with ANTHRACYCLINES.

Molecular weight: 778.95
Formula: C45H54N4O8
CLOGP: 5.94
LIPINSKI: 3
HAC: 12
HDO: 2
TPSA: 133.87
ALOGS: -4.81
ROTB: 10

Status: OFP

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

Drug dosage:

None

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)	11 %	Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability)	27 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	23 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	20 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.87 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	26 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Dec. 23, 1994	FDA	PIERRE FABRE

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
Malignant neoplasm progression	709.74	22.19	359	14148	67765	50522852
Disease progression	538.52	22.19	337	14170	95529	50495088
Metastases to liver	401.87	22.19	167	14340	19937	50570680
Metastases to bone	385.20	22.19	157	14350	17838	50572779
Neutropenia	375.83	22.19	322	14185	147643	50442974
Palmar-plantar erythrodysaesthesia syndrome	290.83	22.19	133	14374	19965	50570652
Metastases to lung	238.63	22.19	97	14410	10923	50579694
Neoplasm progression	211.17	22.19	121	14386	29036	50561581
Metastases to lymph nodes	194.90	22.19	74	14433	6950	50583667
Mucosal inflammation	175.61	22.19	121	14386	40021	50550596
Breast cancer metastatic	157.47	22.19	71	14436	10293	50580324
Metastases to central nervous system	151.70	22.19	71	14436	11211	50579406
Neuropathy peripheral	134.84	22.19	152	14355	96605	50494012
PIK3CA-activated mutation	116.10	22.19	30	14477	780	50589837
Febrile neutropenia	108.94	22.19	137	14370	97530	50493087
Pleural effusion	98.46	22.19	119	14388	81335	50509282
Breast cancer recurrent	90.98	22.19	36	14471	3772	50586845
Ejection fraction decreased	88.49	22.19	59	14448	18461	50572156
Haematotoxicity	85.93	22.19	43	14464	7852	50582765
Osteonecrosis of jaw	80.56	22.19	70	14437	32456	50558161
Metastases to peritoneum	79.12	22.19	30	14477	2803	50587814
Tonsillar disorder	77.40	22.19	23	14484	1011	50589606
Thrombocytopenia	72.95	22.19	131	14376	127542	50463075
Blood uric acid decreased	72.77	22.19	20	14487	662	50589955
Eosinophil percentage increased	66.05	22.19	20	14487	938	50589679
Neurotoxicity	65.73	22.19	45	14462	14695	50575922
Breast cancer	64.16	22.19	70	14437	42820	50547797
Metastases to skin	62.78	22.19	21	14486	1362	50589255
Off label use	62.62	22.19	285	14222	474141	50116476
Myelosuppression	62.02	22.19	42	14465	13475	50577142
Polyneuropathy	61.23	22.19	40	14467	12091	50578526
Ascites	59.78	22.19	62	14445	35799	50554818
Fall	59.30	22.19	12	14495	334920	50255697
Nasal disorder	59.30	22.19	23	14484	2285	50588332
Bone marrow failure	55.74	22.19	53	14454	27571	50563046
EGFR gene mutation	54.43	22.19	13	14494	242	50590375
Neutropenic sepsis	48.89	22.19	37	14470	14110	50576507
Drug hypersensitivity	48.79	22.19	7	14500	251003	50339614
Death	47.00	22.19	201	14306	325178	50265439
Osteonecrosis	43.16	22.19	42	14465	22475	50568142
Decreased appetite	43.07	22.19	141	14366	200782	50389835
Joint swelling	42.94	22.19	9	14498	245277	50345340
Tumour marker increased	42.03	22.19	21	14486	3819	50586798
Vessel puncture site bruise	40.44	22.19	11	14496	350	50590267
Second primary malignancy	40.37	22.19	25	14482	6889	50583728
Hepatotoxicity	39.95	22.19	44	14463	27182	50563435
Leukopenia	39.42	22.19	70	14437	67458	50523159
Peripheral sensory neuropathy	38.91	22.19	24	14483	6567	50584050
Lymphangiosis carcinomatosa	38.28	22.19	14	14493	1182	50589435
Blood creatinine decreased	36.92	22.19	21	14486	4955	50585662
Therapy partial responder	36.39	22.19	23	14484	6568	50584049
Gastrointestinal toxicity	35.40	22.19	20	14487	4657	50585960
Hyperchlorhydria	34.95	22.19	14	14493	1514	50589103
Superior vena cava syndrome	34.74	22.19	11	14496	599	50590018
Stomatitis	34.34	22.19	84	14423	101260	50489357
Injection site extravasation	33.67	22.19	23	14484	7478	50583139
Mediastinum neoplasm	33.62	22.19	7	14500	67	50590550
Hypothalamo-pituitary disorder	33.45	22.19	11	14496	676	50589941
Metastases to chest wall	33.04	22.19	10	14497	468	50590149
Blood lactate dehydrogenase increased	32.91	22.19	34	14473	19528	50571089
Cardiotoxicity	32.62	22.19	22	14485	7005	50583612
Metastases to spine	32.52	22.19	16	14491	2815	50587802
Transaminases	32.10	22.19	7	14500	85	50590532
Metastasis	31.21	22.19	18	14489	4357	50586260
Osteolysis	31.02	22.19	15	14492	2542	50588075
Diarrhoea	31.00	22.19	280	14227	588196	50002421
Pituitary tumour	30.97	22.19	11	14496	854	50589763
Disease recurrence	30.41	22.19	33	14474	20048	50570569
Skin toxicity	30.34	22.19	17	14490	3896	50586721
Nausea	30.05	22.19	321	14186	705077	49885540
Hiccups	29.90	22.19	13	14494	1726	50588891
Arthralgia	29.84	22.19	50	14457	438652	50151965
Pruritus	29.37	22.19	23	14484	283545	50307072
Constipation	29.30	22.19	118	14389	185590	50405027
Hormone receptor positive breast cancer	28.66	22.19	9	14498	477	50590140
Folate deficiency	28.44	22.19	13	14494	1942	50588675
Metastases to meninges	28.14	22.19	13	14494	1989	50588628
Abdominal discomfort	27.72	22.19	16	14491	231625	50358992
Maternal exposure during pregnancy	27.66	22.19	6	14501	159772	50430845
Acquired gene mutation	27.61	22.19	10	14497	821	50589796
Lymphoedema	27.48	22.19	22	14485	9100	50581517
Gene mutation	26.85	22.19	11	14496	1260	50589357
Pancytopenia	26.72	22.19	68	14439	83962	50506655
Urticaria	26.63	22.19	3	14504	129558	50461059
Drug ineffective	26.60	22.19	133	14374	819200	49771417
Metastases to pleura	26.56	22.19	11	14496	1295	50589322
Sinusitis	26.47	22.19	8	14499	170550	50420067
Hypertransaminasaemia	26.14	22.19	15	14492	3596	50587021
Condition aggravated	26.13	22.19	28	14479	297030	50293587
Vascular device infection	25.97	22.19	16	14491	4368	50586249
Metastatic neoplasm	25.60	22.19	15	14492	3739	50586878
Dermatitis exfoliative generalised	25.38	22.19	14	14493	3112	50587505
Gingival bleeding	25.24	22.19	23	14484	11330	50579287
Jaw operation	24.48	22.19	9	14498	771	50589846
Diffuse large B-cell lymphoma recurrent	24.45	22.19	11	14496	1584	50589033
Toothache	24.25	22.19	27	14480	16867	50573750
Cardiac cirrhosis	24.13	22.19	6	14501	133	50590484
Hepatic enzyme increased	24.10	22.19	5	14502	137375	50453242
Nail avulsion	23.92	22.19	6	14501	138	50590479
Eosinophil count increased	23.88	22.19	20	14487	8810	50581807
Scintillating scotoma	23.63	22.19	6	14501	145	50590472
Anaemia	23.59	22.19	138	14369	252318	50338299
Body temperature decreased	23.19	22.19	26	14481	16369	50574248
Postictal state	22.76	22.19	9	14498	941	50589676
Mediastinal disorder	22.57	22.19	7	14500	356	50590261
Odynophagia	22.38	22.19	17	14490	6515	50584102

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
Neutropenia	105.98	25.84	100	3261	131611	29439555
Febrile neutropenia	73.00	25.84	76	3285	112164	29459002
Off label use	68.57	25.84	122	3239	300678	29270488
Malignant neoplasm progression	59.01	25.84	56	3305	73803	29497363
Febrile bone marrow aplasia	57.51	25.84	24	3337	7327	29563839
Neutropenic sepsis	52.67	25.84	26	3335	11701	29559465
Disease progression	47.03	25.84	52	3309	81864	29489302
Toxic erythema of chemotherapy	39.72	25.84	7	3354	71	29571095
Myelosuppression	37.47	25.84	21	3340	12206	29558960
Metastases to lung	37.01	25.84	18	3343	7837	29563329
Product use in unapproved indication	34.86	25.84	46	3315	86829	29484337
Neoplasm progression	34.07	25.84	23	3338	18589	29552577
Leukopenia	33.30	25.84	36	3325	55167	29515999
Product leakage	32.97	25.84	8	3353	415	29570751
Interstitial lung disease	31.98	25.84	36	3325	57682	29513484
Hypophosphataemia	30.97	25.84	16	3345	7908	29563258
Pneumonitis	29.75	25.84	25	3336	28019	29543147
Thrombocytopenia	27.07	25.84	52	3309	134771	29436395
Diffuse large B-cell lymphoma refractory	26.80	25.84	8	3353	914	29570252
Metastases to the mediastinum	26.67	25.84	6	3355	223	29570943

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
Malignant neoplasm progression	481.78	20.84	301	13675	112570	64372186
Neutropenia	331.26	20.84	328	13648	239296	64245460
Disease progression	269.37	20.84	232	13744	141448	64343308
Metastases to bone	244.99	20.84	109	13867	20326	64464430
Metastases to lung	210.90	20.84	90	13886	15174	64469582
Metastases to liver	207.35	20.84	102	13874	23839	64460917
Neoplasm progression	194.01	20.84	117	13859	40847	64443909
Palmar-plantar erythrodysaesthesia syndrome	159.30	20.84	91	13885	28728	64456028
Mucosal inflammation	144.77	20.84	115	13861	62469	64422287
Neuropathy peripheral	124.54	20.84	140	13836	117385	64367371
Febrile neutropenia	123.19	20.84	176	13800	187481	64297275
Metastases to lymph nodes	119.06	20.84	51	13925	8666	64476090
Breast cancer metastatic	118.31	20.84	48	13928	7121	64477635
Neutropenic sepsis	106.34	20.84	65	13911	23207	64461549
Metastases to central nervous system	99.19	20.84	52	13924	13860	64470896
Breast cancer recurrent	90.04	20.84	30	13946	2553	64482203
Myelosuppression	89.99	20.84	59	13917	23771	64460985
Tonsillar disorder	84.50	20.84	23	13953	978	64483778
PIK3CA-activated mutation	78.37	20.84	19	13957	506	64484250
Osteonecrosis of jaw	70.98	20.84	63	13913	39762	64444994
Bone marrow failure	64.67	20.84	65	13911	47887	64436869
Off label use	64.43	20.84	289	13687	632517	63852239
Blood uric acid decreased	64.34	20.84	19	13957	1087	64483669
Haematotoxicity	64.02	20.84	38	13938	12858	64471898
Febrile bone marrow aplasia	63.39	20.84	36	13940	11219	64473537
Nasal disorder	60.57	20.84	23	13953	2861	64481895
Ejection fraction decreased	60.50	20.84	50	13926	28657	64456099
Eosinophil percentage increased	59.61	20.84	19	13957	1405	64483351
Thrombocytopenia	59.37	20.84	142	13834	223659	64261097
Metastases to peritoneum	55.96	20.84	23	13953	3524	64481232
EGFR gene mutation	53.45	20.84	13	13963	351	64484405
Fall	48.60	20.84	15	13961	416811	64067945
Therapy partial responder	47.76	20.84	29	13947	10219	64474537
Neurotoxicity	44.20	20.84	41	13935	27363	64457393
Pleural effusion	43.33	20.84	89	13887	126470	64358286
Peripheral sensory neuropathy	42.52	20.84	28	13948	11350	64473406
Vessel puncture site bruise	41.73	20.84	11	13965	413	64484343
Metastases to skin	39.46	20.84	14	13962	1438	64483318
Metastases to spine	39.08	20.84	18	13958	3625	64481131
Polyneuropathy	38.51	20.84	33	13943	19861	64464895
Pancytopenia	38.02	20.84	91	13885	143218	64341538
Hormone receptor positive breast cancer	34.92	20.84	9	13967	309	64484447
Hepatotoxicity	34.61	20.84	43	13933	39919	64444837
Leukopenia	34.41	20.84	71	13905	101171	64383585
Hyperchlorhydria	32.99	20.84	13	13963	1786	64482970
Blood creatinine decreased	32.98	20.84	20	13956	7030	64477726
Injection site extravasation	32.92	20.84	21	13955	8065	64476691
Lymphangiosis carcinomatosa	32.83	20.84	13	13963	1808	64482948
Hypothalamo-pituitary disorder	31.96	20.84	11	13965	1033	64483723
Stomatitis	31.69	20.84	72	13904	109533	64375223
Pituitary tumour	31.34	20.84	11	13965	1095	64483661
Agranulocytosis	31.30	20.84	40	13936	38189	64446567
Disease recurrence	30.71	20.84	36	13940	31474	64453282
Decreased appetite	30.36	20.84	131	13845	281158	64203598
Metastases to the mediastinum	30.30	20.84	9	13967	525	64484231
Nausea	29.98	20.84	280	13696	785520	63699236
Blood lactate dehydrogenase increased	29.30	20.84	36	13940	33042	64451714
Transaminases	28.88	20.84	6	13970	77	64484679
Drug hypersensitivity	28.70	20.84	8	13968	237807	64246949
Mediastinum neoplasm	28.14	20.84	6	13970	88	64484668
Primary mediastinal large B-cell lymphoma	28.07	20.84	5	13971	26	64484730
Constipation	28.03	20.84	111	13865	229226	64255530
Breast cancer	27.91	20.84	33	13943	29115	64455641
Gene mutation	27.83	20.84	12	13964	2070	64482686
Diarrhoea	27.78	20.84	258	13718	722446	63762310
Toxic erythema of chemotherapy	27.61	20.84	7	13969	225	64484531
Gingival bleeding	27.45	20.84	24	13952	14830	64469926
Nail avulsion	27.42	20.84	6	13970	100	64484656
Lower limb fracture	27.30	20.84	23	13953	13522	64471234
Gastrointestinal toxicity	27.24	20.84	16	13960	5306	64479450
Osteonecrosis	27.09	20.84	32	13944	28197	64456559
Arthralgia	26.74	20.84	34	13942	442226	64042530
Nail infection	25.85	20.84	11	13965	1836	64482920
Ascites	25.33	20.84	47	13929	61954	64422802
Hypertransaminasaemia	25.19	20.84	17	13959	7174	64477582
Acquired gene mutation	25.09	20.84	11	13965	1975	64482781
Tumour marker increased	24.88	20.84	13	13963	3437	64481319
Folate deficiency	24.58	20.84	12	13964	2751	64482005
Hypotension	24.39	20.84	28	13948	380946	64103810
Toothache	24.14	20.84	24	13952	17435	64467321
Scintillating scotoma	23.34	20.84	6	13970	204	64484552
Jaw operation	23.24	20.84	8	13968	751	64484005
Cardiac cirrhosis	23.06	20.84	6	13970	214	64484542
Acute myeloid leukaemia	22.90	20.84	29	13947	27434	64457322
Product use in unapproved indication	21.98	20.84	86	13890	176532	64308224
Cardiotoxicity	21.86	20.84	18	13958	10256	64474500
Metastatic neoplasm	21.81	20.84	13	13963	4429	64480327
Osteolysis	21.47	20.84	11	13965	2792	64481964
Joint swelling	21.31	20.84	10	13966	215372	64269384
Gastric neoplasm	21.18	20.84	6	13970	296	64484460
Anaemia	20.91	20.84	147	13829	378533	64106223

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	L01CA04	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS PLANT ALKALOIDS AND OTHER NATURAL PRODUCTS Vinca alkaloids and analogues
FDA CS	M0022674	Vinca Alkaloids
MeSH PA	D050256	Antimitotic Agents
MeSH PA	D000970	Antineoplastic Agents
MeSH PA	D000972	Antineoplastic Agents, Phytogenic
MeSH PA	D050257	Tubulin Modulators
FDA EPC	N0000175612	Vinca Alkaloid
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:47868	photosensitising agent

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Non-small cell lung cancer	indication	254637007	DOID:3908
Kaposi's sarcoma	off-label use	109385007
Neoplasm of endometrium	off-label use	123844007	DOID:1380
Small cell carcinoma of lung	off-label use	254632001	DOID:5409
Metastatic Breast Carcinoma	off-label use
Disorder of lung	contraindication	19829001	DOID:850
Infectious disease	contraindication	40733004
Gastrointestinal perforation	contraindication	51875005
Hepatic failure	contraindication	59927004
Interstitial pneumonia	contraindication	64667001
Intestinal obstruction	contraindication	81060008	DOID:8437
Leukopenia	contraindication	84828003	DOID:615
Gastrointestinal obstruction	contraindication	126765001
Pregnancy, function	contraindication	289908002
Bone marrow depression	contraindication	307762000
Breastfeeding (mother)	contraindication	413712001
Hepatic Metastases	contraindication
Intestinal Ischemic Necrosis	contraindication
Severe Granulocytopenia	contraindication

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	11.32	acidic
pKa2	13.35	acidic
pKa3	8.55	Basic
pKa4	7.39	Basic
pKa5	6.11	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
Tubulin beta	Tumour-associated antigen	P07437 Q9H4B7 Q13885 Q9BVA1 Q13509 P04350 P68371 Q9BUF5 Q3ZCM7	TBB5_HUMAN TBB1_HUMAN TBB2A_HUMAN TBB2B_HUMAN TBB3_HUMAN TBB4A_HUMAN TBB4B_HUMAN TBB6_HUMAN TBB8_HUMAN	INHIBITOR			SCIENTIFIC LITERATURE	SCIENTIFIC LITERATURE
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN		IC50	6	DRUG MATRIX
Substance-K receptor	GPCR	P21452	NK2R_HUMAN		Ki	6.27	DRUG MATRIX

External reference:

ID	Source
4023981	VUID
N0000021986	NUI
D01935	KEGG_DRUG
125317-39-7	SECONDARY_CAS_RN
4020895	VANDF
4023981	VANDF
C0078257	UMLSCUI
CHEBI:480999	CHEBI
GDF	PDB_CHEM_ID
CHEMBL553025	ChEMBL_ID
CHEMBL538943	ChEMBL_ID
CHEMBL3039595	ChEMBL_ID
D000077235	MESH_DESCRIPTOR_UI
DB00361	DRUGBANK_ID
7105	IUPHAR_LIGAND_ID
6054	INN_ID
Q6C979R91Y	UNII
5311497	PUBCHEM_CID
114527	RXNORM
2135	MMSL
46388	MMSL
5676	MMSL
d03810	MMSL
004380	NDDF
004381	NDDF
108792008	SNOMEDCT_US
108794009	SNOMEDCT_US
372541004	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Vinorelbine	HUMAN PRESCRIPTION DRUG LABEL	1	25021-204	INJECTION, SOLUTION	10 mg	INTRAVENOUS	ANDA	27 sections
Vinorelbine	HUMAN PRESCRIPTION DRUG LABEL	1	45963-607	INJECTION, SOLUTION	10 mg	INTRAVENOUS	ANDA	19 sections