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

Stem definitionDrug idCAS RN
vinca alkaloids 2827 71486-22-1

Description:

MoleculeDescription

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:

PropertyValueReference
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:

DateAgencyCompanyOrphan
Dec. 23, 1994 FDA PIERRE FABRE

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients 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 termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients 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 termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients 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:

SourceCodeDescription
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)

DiseaseRelationSNOMED_IDDOID
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 levelDissociation constantType (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:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Tubulin beta Tumour-associated antigen INHIBITOR SCIENTIFIC LITERATURE SCIENTIFIC LITERATURE
Cytochrome P450 3A4 Enzyme IC50 6 DRUG MATRIX
Substance-K receptor GPCR Ki 6.27 DRUG MATRIX

External reference:

IDSource
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:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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