vinorelbine 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 902.70 17.55 486 21071 64440 46600065
Disease progression 692.80 17.55 463 21094 90837 46573668
Metastases to liver 527.72 17.55 231 21326 19354 46645151
Metastases to bone 476.89 17.55 208 21349 17268 46647237
Neutropenia 446.18 17.55 431 21126 142773 46521732
Palmar-plantar erythrodysaesthesia syndrome 402.62 17.55 194 21363 20257 46644248
Breast cancer metastatic 344.69 17.55 154 21403 13524 46650981
Metastases to lung 264.90 17.55 119 21438 10577 46653928
Metastases to central nervous system 216.35 17.55 105 21452 11116 46653389
Metastases to lymph nodes 214.13 17.55 89 21468 6542 46657963
Breast cancer 196.50 17.55 165 21392 45353 46619152
Osteonecrosis 193.18 17.55 130 21427 25614 46638891
Febrile neutropenia 189.86 17.55 226 21331 94401 46570104
Mucosal inflammation 180.12 17.55 147 21410 38829 46625676
Osteonecrosis of jaw 176.57 17.55 138 21419 34264 46630241
Neoplasm progression 165.74 17.55 120 21437 26563 46637942
Haematotoxicity 146.17 17.55 69 21488 6864 46657641
Pseudocirrhosis 129.92 17.55 35 21522 653 46663852
Ejection fraction decreased 128.39 17.55 88 21469 17849 46646656
Neuropathy peripheral 111.57 17.55 171 21386 90722 46573783
Breast cancer recurrent 111.30 17.55 48 21509 3863 46660642
Pleural effusion 110.28 17.55 162 21395 82790 46581715
Metastases to skin 109.90 17.55 36 21521 1344 46663161
Metastases to peritoneum 104.27 17.55 41 21516 2607 46661898
Bone marrow failure 93.26 17.55 90 21467 29579 46634926
Neutropenic sepsis 87.09 17.55 60 21497 12264 46652241
Fall 84.05 17.55 24 21533 329073 46335432
Drug hypersensitivity 81.10 17.55 9 21548 243816 46420689
PIK3CA-activated mutation 78.89 17.55 23 21534 578 46663927
Ascites 77.58 17.55 90 21467 36494 46628011
Tooth extraction 72.91 17.55 50 21507 10143 46654362
Lymphoedema 70.64 17.55 46 21511 8566 46655939
Leukopenia 68.04 17.55 117 21440 68226 46596279
Neurotoxicity 65.98 17.55 53 21504 13664 46650841
Product dose omission issue 65.18 17.55 3 21554 168517 46495988
Tonsillar disorder 56.72 17.55 20 21537 936 46663569
Bone disorder 54.14 17.55 56 21501 19977 46644528
Debridement 53.49 17.55 21 21536 1329 46663176
Thrombocytopenia 49.07 17.55 149 21408 126432 46538073
Metastases to spine 48.29 17.55 24 21533 2670 46661835
Polyneuropathy 47.70 17.55 41 21516 11603 46652902
Therapy partial responder 45.89 17.55 28 21529 4654 46659851
Lymphangiosis carcinomatosa 45.75 17.55 18 21539 1146 46663359
Metastasis 45.40 17.55 27 21530 4285 46660220
Jaw operation 44.77 17.55 16 21541 779 46663726
Vessel puncture site bruise 44.54 17.55 13 21544 328 46664177
Skin toxicity 44.10 17.55 25 21532 3629 46660876
Death 44.03 17.55 285 21272 335263 46329242
Blood uric acid decreased 42.85 17.55 14 21543 518 46663987
Joint swelling 42.52 17.55 12 21545 166061 46498444
Stomatitis 42.50 17.55 96 21461 68201 46596304
Nasal disorder 40.50 17.55 20 21537 2194 46662311
Metastases to chest wall 40.32 17.55 13 21544 461 46664044
Sequestrectomy 40.24 17.55 16 21541 1047 46663458
Peripheral sensory neuropathy 39.39 17.55 29 21528 6574 46657931
Arthralgia 38.94 17.55 68 21489 364535 46299970
Cardiotoxicity 38.92 17.55 29 21528 6693 46657812
Urticaria 37.56 17.55 5 21552 117887 46546618
Tumour marker increased 36.83 17.55 22 21535 3519 46660986
Pruritus 36.36 17.55 35 21522 242317 46422188
Metastases to pleura 36.35 17.55 15 21542 1081 46663424
Eosinophil percentage increased 36.23 17.55 14 21543 849 46663656
Drug ineffective 36.11 17.55 176 21381 677662 45986843
Hypothalamo-pituitary disorder 35.72 17.55 13 21544 667 46663838
Gastrointestinal toxicity 35.19 17.55 23 21534 4308 46660197
Second primary malignancy 35.02 17.55 27 21530 6557 46657948
Metastases to soft tissue 34.47 17.55 9 21548 148 46664357
EGFR gene mutation 34.41 17.55 9 21548 149 46664356
Desmoplastic small round cell tumour 34.30 17.55 9 21548 151 46664354
Metastases to meninges 34.05 17.55 17 21540 1910 46662595
Superior vena cava syndrome 33.80 17.55 12 21545 573 46663932
Axillary pain 33.74 17.55 15 21542 1298 46663207
Off label use 33.59 17.55 294 21263 379547 46284958
Myelosuppression 33.34 17.55 28 21529 7675 46656830
Injection site pain 33.06 17.55 5 21552 107147 46557358
Osteomyelitis 33.05 17.55 46 21511 22337 46642168
Pyrexia 32.42 17.55 273 21284 348529 46315976
Somnolence 32.22 17.55 16 21541 156505 46508000
Invasive ductal breast carcinoma 32.17 17.55 25 21532 6143 46658362
Anaemia 32.12 17.55 215 21342 255564 46408941
Sinusitis 32.07 17.55 10 21547 129758 46534747
Portal hypertension 32.03 17.55 20 21537 3463 46661042
Pituitary tumour 31.97 17.55 13 21544 902 46663603
Metastatic neoplasm 31.46 17.55 20 21537 3573 46660932
Asthma 31.37 17.55 3 21554 91539 46572966
Loss of consciousness 31.30 17.55 6 21551 108232 46556273
Maternal exposure during pregnancy 31.15 17.55 5 21552 102544 46561961
Disease recurrence 30.37 17.55 40 21517 18431 46646074
General physical health deterioration 29.79 17.55 119 21438 115650 46548855
Drug interaction 29.68 17.55 30 21527 203064 46461441
Urinary tract infection 29.47 17.55 35 21522 220231 46444274
Neutrophil count decreased 29.22 17.55 63 21494 43363 46621142
Transaminases 29.17 17.55 7 21550 80 46664425
Decreased appetite 28.71 17.55 170 21387 193666 46470839
Condition aggravated 28.66 17.55 43 21514 245009 46419496
Blood lactate dehydrogenase increased 28.59 17.55 41 21516 20459 46644046
Bone lesion 27.94 17.55 21 21536 4910 46659595
Pneumonitis 27.40 17.55 48 21509 28372 46636133
Dermatitis exfoliative generalised 26.95 17.55 17 21540 2996 46661509
Weight increased 26.76 17.55 22 21535 164451 46500054
Headache 26.69 17.55 122 21435 478230 46186275
Osteolysis 26.58 17.55 16 21541 2596 46661909
Neutropenic infection 26.07 17.55 12 21545 1126 46663379
Constipation 25.98 17.55 153 21404 173944 46490561
Calcium ionised increased 25.62 17.55 7 21550 138 46664367
Hormone receptor positive breast cancer 25.32 17.55 9 21548 431 46664074
Overdose 24.94 17.55 8 21549 101971 46562534
Vomiting 24.71 17.55 318 21239 452476 46212029
Bone sequestrum 24.48 17.55 13 21544 1660 46662845
Gingivitis 23.97 17.55 23 21534 7497 46657008
Feeling abnormal 23.95 17.55 14 21543 125046 46539459
Anal erythema 23.43 17.55 7 21550 192 46664313
Neoplasm malignant 23.06 17.55 40 21517 23459 46641046
Memory impairment 22.98 17.55 4 21553 77333 46587172
Jaw disorder 22.94 17.55 19 21538 5111 46659394
Asthenia 22.57 17.55 231 21326 310844 46353661
Hypotension 22.48 17.55 46 21511 232543 46431962
Ejection fraction abnormal 22.29 17.55 9 21548 613 46663892
Vascular device infection 22.23 17.55 16 21541 3501 46661004
Hepatic failure 21.93 17.55 48 21509 33368 46631137
Jaundice 21.92 17.55 44 21513 28801 46635704
Injection site erythema 21.79 17.55 4 21553 74423 46590082
Ileus paralytic 21.42 17.55 17 21540 4306 46660199
Exposed bone in jaw 21.21 17.55 15 21542 3193 46661312
Exposure during pregnancy 20.88 17.55 12 21545 108200 46556305
Cardiac cirrhosis 20.88 17.55 6 21551 143 46664362
Bone pain 20.83 17.55 58 21499 46832 46617673
Drug resistance 20.32 17.55 32 21525 17336 46647169
Abdominal discomfort 20.23 17.55 24 21533 151141 46513364
Scintillating scotoma 20.20 17.55 6 21551 161 46664344
Diffuse large B-cell lymphoma recurrent 20.17 17.55 11 21546 1481 46663024
Blood creatinine decreased 20.16 17.55 17 21540 4687 46659818
Ectropion 19.89 17.55 6 21551 170 46664335
Malignant pleural effusion 19.84 17.55 13 21544 2445 46662060
Acute myeloid leukaemia 19.76 17.55 30 21527 15748 46648757
Hyperbaric oxygen therapy 19.70 17.55 5 21552 73 46664432
Joint ankylosis 19.66 17.55 8 21549 556 46663949
Pancytopenia 19.18 17.55 84 21473 84974 46579531
Bronchitis 18.73 17.55 13 21544 105966 46558539
Musculoskeletal stiffness 18.72 17.55 11 21546 97982 46566523
Primary mediastinal large B-cell lymphoma 18.55 17.55 4 21553 27 46664478
Recurrent cancer 18.48 17.55 11 21546 1748 46662757
Hyperplasia 18.28 17.55 8 21549 667 46663838
Bone marrow infiltration 18.17 17.55 7 21550 421 46664084
Atrial fibrillation 17.93 17.55 13 21544 103577 46560928
Sensory disturbance 17.79 17.55 25 21532 12242 46652263
Metastases to the mediastinum 17.58 17.55 7 21550 460 46664045

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 166.50 20.43 165 5937 128375 29818001
Neutropenic sepsis 112.14 20.43 52 6050 11357 29935019
Malignant neoplasm progression 89.94 20.43 91 6011 72196 29874180
Febrile neutropenia 77.96 20.43 102 6000 106591 29839785
Leukopenia 75.91 20.43 74 6028 56085 29890291
Interstitial lung disease 71.59 20.43 74 6028 60123 29886253
Disease progression 64.01 20.43 80 6022 79794 29866582
Off label use 58.65 20.43 145 5957 249145 29697231
Radiation pneumonitis 58.35 20.43 20 6082 1976 29944400
Febrile bone marrow aplasia 52.99 20.43 28 6074 8069 29938307
Neoplasm progression 52.24 20.43 37 6065 17986 29928390
Autoimmune neutropenia 41.35 20.43 10 6092 281 29946095
Metastases to central nervous system 38.84 20.43 22 6080 7262 29939114
Non-small cell lung cancer 36.61 20.43 17 6085 3713 29942663
Cytomegalovirus chorioretinitis 35.56 20.43 16 6086 3252 29943124
Metastases to bone 35.55 20.43 23 6079 9635 29936741
Pneumonitis 34.85 20.43 35 6067 27419 29918957
Metastases to lung 34.59 20.43 21 6081 7874 29938502
Extravasation 33.57 20.43 13 6089 1815 29944561
Agranulocytosis 33.56 20.43 31 6071 21911 29924465
Pyrexia 33.32 20.43 133 5969 294356 29652020
Product leakage 29.91 20.43 8 6094 339 29946037
Metastases to the mediastinum 29.46 20.43 7 6095 182 29946194
Pancytopenia 28.33 20.43 57 6045 84995 29861381
Neutropenic colitis 27.75 20.43 12 6090 2218 29944158
Bone marrow failure 27.33 20.43 32 6070 29753 29916623
Hypophosphataemia 26.39 20.43 18 6084 8227 29938149
Lung adenocarcinoma 26.32 20.43 14 6088 4085 29942291
Myelosuppression 25.88 20.43 17 6085 7305 29939071
General physical health deterioration 24.26 20.43 59 6043 99885 29846491
Tracheal fistula 23.41 20.43 5 6097 79 29946297
Thrombocytopenia 23.34 20.43 71 6031 136973 29809403
Autoimmune pancytopenia 22.69 20.43 5 6097 92 29946284
PIK3CA-activated mutation 22.54 20.43 5 6097 95 29946281
Systemic candida 22.27 20.43 11 6091 2753 29943623
Embryonal rhabdomyosarcoma 21.81 20.43 4 6098 27 29946349
Bacterial infection 21.61 20.43 19 6083 12591 29933785
Recall phenomenon 21.47 20.43 7 6095 592 29945784
Streptococcal endocarditis 20.90 20.43 4 6098 35 29946341
Product use in unapproved indication 20.60 20.43 46 6056 73647 29872729

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
FDA EPC N0000175612 Vinca Alkaloid
MeSH PA D050256 Antimitotic Agents
MeSH PA D000970 Antineoplastic Agents
MeSH PA D000972 Antineoplastic Agents, Phytogenic
MeSH PA D050257 Tubulin Modulators
CHEBI has role CHEBI:35610 cytostatic
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

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
C0131965 UMLSCUI
CHEBI:480999 CHEBI
CHEMBL538943 ChEMBL_ID
CHEMBL553025 ChEMBL_ID
CHEMBL3039595 ChEMBL_ID
D000077235 MESH_DESCRIPTOR_UI
6054 INN_ID
Q6C979R91Y UNII
5311497 PUBCHEM_CID
7105 IUPHAR_LIGAND_ID
DB00361 DRUGBANK_ID
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 50742-420 INJECTION 10 mg INTRAVENOUS ANDA 19 sections
Vinorelbine HUMAN PRESCRIPTION DRUG LABEL 1 50742-427 INJECTION 50 mg INTRAVENOUS ANDA 19 sections
NULLVELBINE HUMAN PRESCRIPTION DRUG LABEL 1 64370-532 INJECTION 10 mg INTRAVENOUS NDA 26 sections