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 740.10 22.47 372 14902 73215 56203578
Disease progression 597.55 22.47 365 14909 104808 56171985
Metastases to liver 412.71 22.47 171 15103 21415 56255378
Metastases to bone 398.33 22.47 162 15112 19346 56257447
Neutropenia 392.91 22.47 332 14942 157835 56118958
Breast cancer metastatic 341.81 22.47 136 15138 15333 56261460
Palmar-plantar erythrodysaesthesia syndrome 298.14 22.47 135 15139 20930 56255863
Metastases to lung 251.79 22.47 101 15173 11617 56265176
Neoplasm progression 214.77 22.47 124 15150 31892 56244901
Metastases to lymph nodes 198.49 22.47 75 15199 7348 56269445
Mucosal inflammation 188.81 22.47 127 15147 42683 56234110
Breast cancer 166.95 22.47 124 15150 48709 56228084
Metastases to central nervous system 159.77 22.47 74 15200 12062 56264731
Neuropathy peripheral 142.60 22.47 157 15117 102736 56174057
PIK3CA-activated mutation 117.51 22.47 31 15243 927 56275866
Febrile neutropenia 114.42 22.47 142 15132 105403 56171390
Pleural effusion 99.09 22.47 119 15155 85361 56191432
Breast cancer recurrent 97.56 22.47 38 15236 4037 56272756
Osteonecrosis of jaw 92.79 22.47 75 15199 33283 56243510
Haematotoxicity 91.65 22.47 45 15229 8338 56268455
Ejection fraction decreased 90.14 22.47 60 15214 19781 56257012
Metastases to peritoneum 89.98 22.47 33 15241 2971 56273822
Thrombocytopenia 78.46 22.47 136 15138 136088 56140705
Tonsillar disorder 77.45 22.47 23 15251 1067 56275726
Myelosuppression 72.64 22.47 50 15224 17405 56259388
Blood uric acid decreased 71.97 22.47 20 15254 730 56276063
Eosinophil percentage increased 66.21 22.47 20 15254 984 56275809
Polyneuropathy 65.47 22.47 42 15232 13008 56263785
Neurotoxicity 65.15 22.47 45 15229 15750 56261043
Ascites 63.90 22.47 64 15210 37480 56239313
Metastases to skin 62.82 22.47 21 15253 1437 56275356
Fall 60.16 22.47 12 15262 357498 55919295
Nasal disorder 58.02 22.47 23 15251 2559 56274234
Bone marrow failure 57.16 22.47 53 15221 28233 56248560
Off label use 55.02 22.47 296 14978 555884 55720909
EGFR gene mutation 53.52 22.47 13 15261 276 56276517
Death 52.50 22.47 207 15067 341219 55935574
Drug hypersensitivity 51.25 22.47 7 15267 275198 56001595
Neutropenic sepsis 50.58 22.47 38 15236 15147 56261646
Joint swelling 50.28 22.47 9 15265 289791 55987002
Osteonecrosis 44.03 22.47 42 15232 23173 56253620
Tumour marker increased 43.83 22.47 22 15252 4271 56272522
Decreased appetite 42.14 22.47 143 15131 219088 56057705
Skin toxicity 41.57 22.47 21 15253 4132 56272661
Therapy partial responder 41.40 22.47 26 15248 7759 56269034
Hepatotoxicity 40.43 22.47 46 15228 31107 56245686
Second primary malignancy 40.06 22.47 25 15249 7377 56269416
Leukopenia 39.71 22.47 70 15204 70870 56205923
Vessel puncture site bruise 39.23 22.47 11 15263 415 56276378
Peripheral sensory neuropathy 38.93 22.47 24 15250 6932 56269861
Hiccups 38.79 22.47 16 15258 1972 56274821
Lymphangiosis carcinomatosa 38.44 22.47 14 15260 1235 56275558
Blood creatinine decreased 37.26 22.47 21 15253 5145 56271648
Arthralgia 35.29 22.47 51 15223 501618 55775175
Hyperchlorhydria 34.94 22.47 14 15260 1601 56275192
Abdominal discomfort 34.58 22.47 16 15258 277258 55999535
Cardiotoxicity 34.41 22.47 23 15251 7627 56269166
Joint neoplasm 34.39 22.47 7 15267 63 56276730
Superior vena cava syndrome 34.38 22.47 11 15263 655 56276138
Metastatic neoplasm 34.02 22.47 18 15256 3895 56272898
Gastrointestinal toxicity 33.84 22.47 21 15253 6135 56270658
Hypothalamo-pituitary disorder 33.84 22.47 11 15263 689 56276104
Mediastinum neoplasm 33.81 22.47 7 15267 69 56276724
Soft tissue neoplasm 33.54 22.47 7 15267 72 56276721
Metastases to meninges 33.51 22.47 15 15259 2255 56274538
Injection site extravasation 33.00 22.47 23 15251 8161 56268632
Hormone receptor positive breast cancer 32.91 22.47 10 15264 502 56276291
Blood lactate dehydrogenase increased 32.90 22.47 34 15240 20641 56256152
Metastases to chest wall 32.81 22.47 10 15264 507 56276286
Maternal exposure during pregnancy 32.61 22.47 6 15268 189547 56087246
Metastases to spine 32.53 22.47 16 15258 2973 56273820
Transaminases 32.48 22.47 7 15267 85 56276708
Disease recurrence 32.27 22.47 36 15238 23824 56252969
Diarrhoea 32.06 22.47 288 14986 638219 55638574
Desmoplastic small round cell tumour 31.88 22.47 8 15266 195 56276598
Invasive ductal breast carcinoma 31.86 22.47 21 15253 6805 56269988
Osteolysis 31.50 22.47 15 15259 2598 56274195
Pituitary tumour 31.39 22.47 11 15263 868 56275925
Acquired gene mutation 31.29 22.47 11 15263 876 56275917
Metastasis 30.64 22.47 18 15256 4766 56272027
Constipation 30.60 22.47 122 15152 201821 56074972
Sinusitis 30.46 22.47 8 15266 197573 56079220
Diffuse large B-cell lymphoma recurrent 30.46 22.47 13 15261 1744 56275049
Hepatic enzyme increased 30.41 22.47 5 15269 171379 56105414
Pruritus 30.17 22.47 25 15249 316598 55960195
Metastases to pleura 29.97 22.47 12 15262 1370 56275423
Nail infection 29.87 22.47 14 15260 2339 56274454
Nausea 29.79 22.47 327 14947 763851 55512942
Condition aggravated 29.59 22.47 30 15244 344868 55931925
Urticaria 28.58 22.47 3 15271 144673 56132120
Jaw operation 27.99 22.47 10 15264 835 56275958
Stomatitis 27.91 22.47 84 15190 120726 56156067
Pancytopenia 27.80 22.47 69 15205 88646 56188147
Folate deficiency 27.78 22.47 13 15261 2164 56274629
Anaemia 26.72 22.47 143 15131 267368 56009425
Musculoskeletal stiffness 26.70 22.47 5 15269 156002 56120791
Asthenia 26.30 22.47 171 15103 342802 55933991
Gene mutation 26.04 22.47 11 15263 1438 56275355
Gingival bleeding 25.79 22.47 23 15251 11643 56265150
Lymphoedema 25.78 22.47 22 15252 10508 56266285
Dermatitis exfoliative generalised 24.93 22.47 14 15260 3406 56273387
Cardiac cirrhosis 24.46 22.47 6 15268 133 56276660
Drug resistance 24.42 22.47 29 15245 20513 56256280
Toothache 24.22 22.47 27 15247 17853 56258940
Nail avulsion 24.00 22.47 6 15268 144 56276649
Scintillating scotoma 23.77 22.47 6 15268 150 56276643
Eosinophil count increased 23.32 22.47 20 15254 9617 56267176
Weight increased 23.31 22.47 17 15257 229686 56047107
Hypertransaminasaemia 23.23 22.47 15 15259 4692 56272101
Vascular device infection 23.22 22.47 16 15258 5574 56271219
Postictal state 23.12 22.47 9 15265 954 56275839
Mediastinal disorder 22.85 22.47 7 15267 361 56276432
Odynophagia 22.56 22.47 17 15257 6801 56269992

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 116.53 26.28 109 3536 140255 31553444
Febrile neutropenia 72.23 26.28 79 3566 121770 31571929
Disease progression 66.77 26.28 66 3579 90398 31603301
Off label use 64.51 26.28 130 3515 347144 31346555
Malignant neoplasm progression 62.71 26.28 60 3585 78938 31614761
Neutropenic sepsis 59.94 26.28 29 3616 12350 31681349
Febrile bone marrow aplasia 55.72 26.28 24 3621 7822 31685877
Pneumonitis 46.72 26.28 34 3611 30618 31663081
Neoplasm progression 39.11 26.28 26 3619 20246 31673453
Myelosuppression 38.48 26.28 23 3622 14897 31678802
Toxic erythema of chemotherapy 37.97 26.28 7 3638 92 31693607
Metastases to lung 35.61 26.28 18 3627 8404 31685295
Leukopenia 33.28 26.28 37 3608 57791 31635908
Product use in unapproved indication 32.58 26.28 48 3597 99123 31594576
Product leakage 32.20 26.28 8 3637 453 31693246
Interstitial lung disease 29.82 26.28 36 3609 61367 31632332
Hypophosphataemia 29.71 26.28 16 3629 8498 31685201
Diffuse large B-cell lymphoma refractory 29.66 26.28 9 3636 1074 31692625
Agranulocytosis 28.85 26.28 22 3623 21225 31672474
Pancytopenia 28.28 26.28 42 3603 87274 31606425
Thrombocytopenia 26.91 26.28 54 3591 142693 31551006

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 505.06 20.68 315 14550 121424 70792155
Neutropenia 348.53 20.68 343 14522 256813 70656766
Disease progression 323.04 20.68 265 14600 156407 70757172
Metastases to bone 242.13 20.68 110 14755 22266 70891313
Breast cancer metastatic 223.49 20.68 83 14782 10063 70903516
Metastases to lung 213.67 20.68 92 14773 16392 70897187
Metastases to liver 203.03 20.68 102 14763 25776 70887803
Neoplasm progression 202.18 20.68 123 14742 45105 70868474
Palmar-plantar erythrodysaesthesia syndrome 163.38 20.68 93 14772 30154 70883425
Mucosal inflammation 150.54 20.68 120 14745 67730 70845849
Neuropathy peripheral 127.99 20.68 145 14720 126751 70786828
Febrile neutropenia 124.83 20.68 182 14683 204136 70709443
Metastases to lymph nodes 121.13 20.68 52 14813 9186 70904393
Neutropenic sepsis 114.69 20.68 69 14796 24761 70888818
Myelosuppression 102.41 20.68 69 14796 30076 70883503
Breast cancer 100.35 20.68 71 14794 33478 70880101
Metastases to central nervous system 99.83 20.68 53 14812 14981 70898598
Breast cancer recurrent 96.66 20.68 32 14833 2761 70910818
Tonsillar disorder 83.24 20.68 23 14842 1071 70912508
Osteonecrosis of jaw 81.37 20.68 68 14797 40934 70872645
PIK3CA-activated mutation 77.32 20.68 19 14846 555 70913024
Haematotoxicity 71.01 20.68 41 14824 13633 70899946
Bone marrow failure 65.30 20.68 65 14800 48945 70864634
Ejection fraction decreased 65.17 20.68 53 14812 30709 70882870
Blood uric acid decreased 63.43 20.68 19 14846 1181 70912398
Thrombocytopenia 62.71 20.68 148 14717 238962 70674617
Febrile bone marrow aplasia 62.38 20.68 36 14829 11955 70901624
Metastases to peritoneum 61.86 20.68 25 14840 3794 70909785
Eosinophil percentage increased 59.89 20.68 19 14846 1431 70912148
Nasal disorder 58.21 20.68 23 14842 3291 70910288
Off label use 55.83 20.68 304 14561 742756 70170823
Therapy partial responder 53.32 20.68 33 14832 12441 70901138
EGFR gene mutation 52.31 20.68 13 14852 398 70913181
Fall 50.90 20.68 15 14850 444081 70469498
Pancytopenia 46.81 20.68 100 14765 151007 70762572
Pleural effusion 43.56 20.68 90 14775 132774 70780805
Pneumonitis 42.86 20.68 55 14810 54542 70859037
Metastases to skin 42.62 20.68 15 14850 1556 70912023
Neurotoxicity 42.41 20.68 41 14824 29785 70883794
Peripheral sensory neuropathy 41.78 20.68 28 14837 12082 70901497
Vessel puncture site bruise 40.59 20.68 11 14854 476 70913103
Hormone receptor positive breast cancer 39.72 20.68 10 14855 323 70913256
Polyneuropathy 39.37 20.68 34 14831 21381 70892198
Metastases to spine 38.80 20.68 18 14847 3811 70909768
Joint neoplasm 36.19 20.68 7 14858 63 70913516
Hepatotoxicity 35.61 20.68 45 14820 43941 70869638
Leukopenia 34.70 20.68 72 14793 106488 70807091
Invasive ductal breast carcinoma 34.43 20.68 19 14846 5790 70907789
Nail infection 34.31 20.68 14 14851 2177 70911402
Soft tissue neoplasm 34.28 20.68 7 14858 85 70913494
Agranulocytosis 33.85 20.68 42 14823 40256 70873323
Hyperchlorhydria 33.08 20.68 13 14852 1833 70911746
Blood creatinine decreased 32.83 20.68 20 14845 7329 70906250
Desmoplastic small round cell tumour 32.74 20.68 8 14857 228 70913351
Lymphangiosis carcinomatosa 32.71 20.68 13 14852 1888 70911691
Injection site extravasation 32.06 20.68 21 14844 8725 70904854
Hypothalamo-pituitary disorder 31.80 20.68 11 14854 1084 70912495
Drug hypersensitivity 31.66 20.68 8 14857 262451 70651128
Nausea 31.61 20.68 294 14571 851794 70061785
Pituitary tumour 31.26 20.68 11 14854 1140 70912439
Arthralgia 30.96 20.68 36 14829 503354 70410225
Metastases to the mediastinum 30.44 20.68 9 14856 535 70913044
Metastatic neoplasm 29.76 20.68 16 14849 4632 70908947
Disease recurrence 29.69 20.68 38 14827 37565 70876014
Transaminases 29.08 20.68 6 14859 77 70913502
Blood lactate dehydrogenase increased 28.53 20.68 36 14829 35091 70878488
Mediastinum neoplasm 28.21 20.68 6 14859 90 70913489
Acquired gene mutation 28.12 20.68 12 14853 2086 70911493
Constipation 28.11 20.68 116 14749 252322 70661257
Decreased appetite 27.85 20.68 132 14733 304648 70608931
Non-small cell lung cancer recurrent 27.67 20.68 6 14859 99 70913480
Gingival bleeding 27.62 20.68 24 14841 15208 70898371
Gastrointestinal toxicity 27.51 20.68 17 14848 6388 70907191
Nail avulsion 27.29 20.68 6 14859 106 70913473
Toxic erythema of chemotherapy 27.26 20.68 7 14858 245 70913334
Osteonecrosis 27.11 20.68 32 14833 29128 70884451
Gene mutation 27.11 20.68 12 14853 2279 70911300
Tumour marker increased 26.96 20.68 14 14851 3780 70909799
Jaw operation 26.81 20.68 9 14856 810 70912769
Joint swelling 26.44 20.68 10 14855 253201 70660378
Diarrhoea 26.41 20.68 265 14600 783076 70130503
Stomatitis 25.80 20.68 72 14793 128439 70785140
Poor peripheral circulation 25.16 20.68 13 14852 3472 70910107
Non-small cell lung cancer 25.13 20.68 16 14849 6331 70907248
Ascites 24.81 20.68 48 14817 67499 70846080
Hypotension 24.76 20.68 29 14836 404352 70509227
Drug resistance 24.67 20.68 35 14830 38155 70875424
Vaginal discharge 24.59 20.68 14 14851 4529 70909050
Folate deficiency 23.91 20.68 12 14853 3018 70910561
Primary mediastinal large B-cell lymphoma 23.76 20.68 5 14860 71 70913508
Lower limb fracture 23.73 20.68 23 14842 16749 70896830
Toothache 23.72 20.68 24 14841 18406 70895173
Scintillating scotoma 23.45 20.68 6 14859 207 70913372
Skin toxicity 23.30 20.68 16 14849 7182 70906397
Cardiotoxicity 23.28 20.68 19 14846 11051 70902528
Cardiac cirrhosis 23.15 20.68 6 14859 218 70913361
Hypertransaminasaemia 22.37 20.68 17 14848 8926 70904653
Cough 22.20 20.68 130 14735 325247 70588332
Nail disorder 22.15 20.68 18 14847 10406 70903173
Asthenia 21.69 20.68 167 14698 457499 70456080
Urticaria 21.62 20.68 4 14861 163045 70750534
Acute myeloid leukaemia 20.94 20.68 29 14836 30911 70882668
Anaemia 20.69 20.68 150 14715 403273 70510306

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 | Suggest Off label Use Form| |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
Vinorelbine HUMAN PRESCRIPTION DRUG LABEL 1 45963-607 INJECTION, SOLUTION 10 mg INTRAVENOUS ANDA 19 sections