Rimegepant
Identification
- Summary
Rimegepant is an oral CGRP receptor antagonist used for the acute treatment of migraines with or without aura in adults.
- Brand Names
- Nurtec
- Generic Name
- Rimegepant
- DrugBank Accession Number
- DB12457
- Background
Rimegepant is an oral antagonist of the CGRP receptor developed by Biohaven Pharmaceuticals.5 It received FDA approval on February 27, 2020 for the acute treatment migraine headache,7 and was subsequently approved by the European Commission in April 2022 for both the treatment and prevention of migraines.10 While several parenteral antagonists of CGRP and its receptor have been approved for migraine therapy (e.g. erenumab, fremanezumab, galcanezumab), rimegepant and ubrogepant were the only CGRP antagonists that possessed oral bioavailability2 until the approval of atogepant in 2021.9
The current standard of migraine therapy involves abortive treatment with "triptans", such as sumatriptan, but these medications are contraindicated in patients with pre-existing cerebrovascular and cardiovascular disease due to their vasoconstrictive properties.2 Antagonism of the CGRP pathway has become an attractive target for migraine therapy as, unlike the triptans, oral CGRP antagonists have no observed vasoconstrictive properties and are therefore safer for use in patients with contraindications to standard therapy.1,2
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 534.568
Monoisotopic: 534.219095112 - Chemical Formula
- C28H28F2N6O3
- Synonyms
- Rimegepant
- External IDs
- BMS 927711
- BMS-927711
Pharmacology
- Indication
Rimegepant is indicated for the acute treatment of migraine with or without aura in adults. Rimegepant is also indicated for the prevention of episodic migraine in adults.6
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prevention of Episodic migraine •••••••••••• ••••• ••••••• •••••• •••••••••••••• Treatment of Migraine with aura •••••••••••• ••••• ••••••• •••••• •••••••••••••• Treatment of Migraine without aura •••••••••••• ••••• ••••••• •••••• •••••••••••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Rimegepant helps to abort migraine headaches by preventing the activity of a pronociceptive molecule that has been implicated in migraine pathophysiology.6 It is intended for use as an abortive migraine therapy and therefore has a relatively rapid onset of effect, with most efficacy trials evaluating for effect at the 2 hour mark.6
Rimegepant does not require dose adjustment in patients with mild, moderate, or severe renal impairment,6 nor does it require dose adjustment in patients with mild or moderate hepatic impairment. In clinical trials, plasma concentrations of rimegepant were significantly higher in patients with severe (i.e. Child-Pugh C) hepatic impairment - it should therefore be avoided in this population.6 Hypersensitivity reactions have occurred during clinical studies and patients should be made aware of this possibility. Rimegepant should be discontinued immediately if hypersensitivity reaction occurs.6
- Mechanism of action
The currently accepted theory of migraine pathophysiology considers dysfunction of the central nervous system, in particular the trigeminal ganglion, to be the root cause behind the condition.2 Activation of the trigeminal ganglion triggers the stimulation of trigeminal afferents that project to the spinal cord and synapse on various pain-sensing intra- and extracranial structures, such as the dura mater. Pain signals are then further transmitted via second-order ascending neurons to the brainstem, hypothalamus, and thalamic nuclei, and from there to several cortical regions (e.g. auditory, visual, motor cortices).2 The trigeminal ganglion appears to amplify and perpetuate the migraine headache pain through the activation of perivascular fibers and the release of molecules involved in pain generation, such as calcitonin gene-related peptide (CGRP).2
The α-isoform of CGRP, expressed in primary sensory neurons, is a potent vasodilator and has been implicated in migraine pathogenesis - CGRP levels are acutely elevated during migraine attacks, return to normal following treatment with triptan medications, and intravenous infusions of CGRP have been shown to trigger migraine-like headaches in migraine patients. In addition to its vasodilatory properties, CGRP appears to be a pronociceptive factor that modulates neuronal excitability to facilitate pain responses.3
Rimegepant is an antagonist of the calcitonin gene-related peptide receptor1 - it competes with CGRP for occupancy at these receptors, preventing the actions of CGRP and its ability to amplify and perpetuate migraine headache pain, ultimately terminating the headache.3
Target Actions Organism ACalcitonin gene-related peptide type 1 receptor antagonistHumans - Absorption
The absolute oral bioavailability of rimegepant is approximately 64%.6 Following oral administration of the orally disintegrating tablet, maximum plasma concentrations were achieved at 1.5 hours (Tmax).6
When administered with a high-fat meal, Tmax is delayed by 1 hour, Cmax is decreased by 42-53%, and AUC is decreased by 32-38%.6 The clinical significance of this difference in pharmacokinetics is unknown.
- Volume of distribution
At steady state, the volume of distribution is approximately 120 L.6
- Protein binding
Rimegepant is approximately 96% plasma protein-bound.6 The specific proteins to which rimegepant binds have not been elucidated.
- Metabolism
Rimegepant is metabolized by CYP3A4 and, to a lesser extent, CYP2C9.6 Specific metabolites of rimegepant have not been characterized and no major metabolites have been detected in plasma.6 Approximately 77% of an administered dose is eliminated unchanged,6 suggesting metabolism is likely to be a minor means of drug elimination.
- Route of elimination
Following oral administration of radiolabeled rimegepant in healthy subjects, 78% of the administered radioactivity was recovered in feces and 24% in urine.6 Unchanged parent drug was the major component in each, comprising 42% and 51% of the recovered doses, respectively.
- Half-life
The elimination half-life in healthy subjects is approximately 11 hours.6
- Clearance
Not Available
- Adverse Effects
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- Toxicity
There is no specific antidote for rimegepant overdosage and clinical experience is limited.6 Treatment should consist of general supportive and symptomatic measures including monitoring of vital signs and general observation. Hemodialysis is unlikely to be of benefit given rimegepant's high serum protein binding.6
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Rimegepant can be increased when it is combined with Abametapir. Abemaciclib The serum concentration of Rimegepant can be increased when it is combined with Abemaciclib. Abrocitinib The serum concentration of Rimegepant can be increased when it is combined with Abrocitinib. Acetaminophen The metabolism of Rimegepant can be increased when combined with Acetaminophen. Adagrasib The serum concentration of Rimegepant can be increased when it is combined with Adagrasib. - Food Interactions
- Take with or without food. Pharmacokinetics may be altered when administered with high-fat meals, but the clinical relevance of these effects is unknown.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Rimegepant sulfate 1383NM3Q0H 1374024-48-2 SOGUOEZRYKUOHR-CQZKMDJHSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Nurtec ODT Tablet, orally disintegrating 75 mg/1 Oral Pfizer Laboratories Div Pfizer Inc 2020-03-05 Not applicable US Nurtec ODT Tablet, orally disintegrating 75 mg Oral Pfizer Canada Ulc Not applicable Not applicable Canada Nurtec ODT Tablet, orally disintegrating 75 mg/1 Oral Pfizer Laboratories Div Pfizer Inc 2020-03-05 Not applicable US Vydura Tablet 75 mg Oral Pfizer Europe Ma Eeig 2022-05-17 Not applicable EU Vydura Tablet 75 mg Oral Pfizer Europe Ma Eeig 2022-06-07 Not applicable EU
Categories
- ATC Codes
- N02CD06 — Rimegepant
- Drug Categories
- Analgesics
- Antimigraine Preparations
- BCRP/ABCG2 Substrates
- Calcitonin Gene-Related Peptide (CGRP) Antagonists
- Calcitonin Gene-Related Peptide Receptor Antagonists
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (weak)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- MATE 1 Inhibitors
- MATE inhibitors
- Migraine Disorders
- Nervous System
- OAT3/SLC22A8 Inhibitors
- OATP1B1/SLCO1B1 Inhibitors
- OATP1B3 inhibitors
- OCT2 Inhibitors
- P-glycoprotein substrates
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as imidazopyridines. These are organic polycyclic compounds containing an imidazole ring fused to a pyridine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Imidazopyridines
- Sub Class
- Not Available
- Direct Parent
- Imidazopyridines
- Alternative Parents
- Piperidinecarboxylic acids / Fluorobenzenes / Aralkylamines / Pyridines and derivatives / N-substituted imidazoles / Aryl fluorides / Heteroaromatic compounds / Carbamate esters / Ureas / Azacyclic compounds show 5 more
- Substituents
- Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Azole / Benzenoid / Carbamic acid ester / Carbonyl group show 21 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 997WVV895X
- CAS number
- 1289023-67-1
- InChI Key
- KRNAOFGYEFKHPB-ANJVHQHFSA-N
- InChI
- InChI=1S/C28H28F2N6O3/c29-20-6-1-4-17(23(20)30)18-8-9-22(25-19(24(18)31)5-2-12-32-25)39-28(38)35-14-10-16(11-15-35)36-21-7-3-13-33-26(21)34-27(36)37/h1-7,12-13,16,18,22,24H,8-11,14-15,31H2,(H,33,34,37)/t18-,22+,24-/m0/s1
- IUPAC Name
- (5S,6S,9R)-5-amino-6-(2,3-difluorophenyl)-5H,6H,7H,8H,9H-cyclohepta[b]pyridin-9-yl 4-{2-oxo-1H,2H,3H-imidazo[4,5-b]pyridin-1-yl}piperidine-1-carboxylate
- SMILES
- N[C@H]1[C@@H](CC[C@@H](OC(=O)N2CCC(CC2)N2C(=O)NC3=NC=CC=C23)C2=C1C=CC=N2)C1=C(F)C(F)=CC=C1
References
- Synthesis Reference
Luo G, Chen L, Conway CM, Kostich W, Macor JE, Dubowchik GM: Asymmetric Synthesis of Heterocyclic Analogues of a CGRP Receptor Antagonist for Treating Migraine. Org Lett. 2015 Dec 18;17(24):5982-5.
- General References
- Lipton RB, Croop R, Stock EG, Stock DA, Morris BA, Frost M, Dubowchik GM, Conway CM, Coric V, Goadsby PJ: Rimegepant, an Oral Calcitonin Gene-Related Peptide Receptor Antagonist, for Migraine. N Engl J Med. 2019 Jul 11;381(2):142-149. doi: 10.1056/NEJMoa1811090. [Article]
- Negro A, Martelletti P: Gepants for the treatment of migraine. Expert Opin Investig Drugs. 2019 Jun;28(6):555-567. doi: 10.1080/13543784.2019.1618830. Epub 2019 May 17. [Article]
- Martelletti P, Giamberardino MA: Advances in orally administered pharmacotherapy for the treatment of migraine. Expert Opin Pharmacother. 2019 Feb;20(2):209-218. doi: 10.1080/14656566.2018.1549223. Epub 2018 Nov 26. [Article]
- Luo G, Chen L, Conway CM, Kostich W, Macor JE, Dubowchik GM: Asymmetric Synthesis of Heterocyclic Analogues of a CGRP Receptor Antagonist for Treating Migraine. Org Lett. 2015 Dec 18;17(24):5982-5. doi: 10.1021/acs.orglett.5b02921. Epub 2015 Dec 9. [Article]
- BiopharmaDive: 5 FDA Approval Decisions to Watch in the 1st Quarter [Link]
- FDA Approved Drug Products: Nurtec ODT (rimegepant) orally disintegrating tablets [Link]
- Biohaven Pharmaceuticals Press Release: Nurtec ODT FDA Approval [Link]
- CaymanChem: Rimegepant MSDS [Link]
- PR Newswire: FDA Approves QULIPTA™ (atogepant), the First and Only Oral CGRP Receptor Antagonist Specifically Developed for the Preventive Treatment of Migraine [Link]
- Pfizer: Pfizer and Biohaven’s VYDURA® (Rimegepant) Granted First Ever Marketing Authorization by European Commission for Both Acute Treatment of Migraine and Prophylaxis of Episodic Migraine [Link]
- External Links
- PubChem Compound
- 51049968
- PubChem Substance
- 347828697
- ChemSpider
- 27289072
- BindingDB
- 50400098
- 2282307
- ChEMBL
- CHEMBL2178422
- ZINC
- ZINC000068267814
- Wikipedia
- Rimegepant
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Episodic Migraine / Migraine / Phonophobia / Photophobia 1 4 Completed Treatment Episodic Migraine / Migraine 1 4 Completed Treatment Pain 1 4 Not Yet Recruiting Treatment Irritable Bowel Syndrome (IBS) 1 4 Recruiting Prevention Migraine 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, orally disintegrating Oral 75 mg Tablet, orally disintegrating Oral 75 mg/1 Tablet Oral 75 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8314117 No 2012-11-20 2031-02-22 US US8759372 No 2014-06-24 2033-02-25 US US11083724 No 2021-08-10 2039-03-25 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Slightly soluble FDA label - Predicted Properties
Property Value Source Water Solubility 0.0755 mg/mL ALOGPS logP 2.68 ALOGPS logP 2.95 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 10.7 Chemaxon pKa (Strongest Basic) 8.95 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 113.68 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 139.58 m3·mol-1 Chemaxon Polarizability 54.23 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 221.11198 predictedDeepCCS 1.0 (2019) [M+H]+ 223.2506 predictedDeepCCS 1.0 (2019) [M+Na]+ 229.1376 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Receptor for calcitonin-gene-related peptide (CGRP) together with RAMP1 and receptor for adrenomedullin together with RAMP3 (By similarity). Receptor for adrenomedullin together with RAMP2. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
- Specific Function
- Adrenomedullin receptor activity
- Gene Name
- CALCRL
- Uniprot ID
- Q16602
- Uniprot Name
- Calcitonin gene-related peptide type 1 receptor
- Molecular Weight
- 52928.98 Da
References
- Lipton RB, Croop R, Stock EG, Stock DA, Morris BA, Frost M, Dubowchik GM, Conway CM, Coric V, Goadsby PJ: Rimegepant, an Oral Calcitonin Gene-Related Peptide Receptor Antagonist, for Migraine. N Engl J Med. 2019 Jul 11;381(2):142-149. doi: 10.1056/NEJMoa1811090. [Article]
- Negro A, Martelletti P: Gepants for the treatment of migraine. Expert Opin Investig Drugs. 2019 Jun;28(6):555-567. doi: 10.1080/13543784.2019.1618830. Epub 2019 May 17. [Article]
- FDA Approved Drug Products: Nurtec ODT (rimegepant) orally disintegrating tablets [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- Curator comments
- Rimegepant is a weak inhibitor of CYP3A4 that exhibits time-dependent inhibition.
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- FDA Approved Drug Products: Nurtec ODT (rimegepant) orally disintegrating tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- FDA Approved Drug Products: Nurtec ODT (rimegepant) orally disintegrating tablets [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- FDA Approved Drug Products: Nurtec ODT (rimegepant) orally disintegrating tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
References
- FDA Approved Drug Products: Nurtec ODT (rimegepant) orally disintegrating tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- FDA Approved Drug Products: Nurtec ODT (rimegepant) orally disintegrating tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- FDA Approved Drug Products: Nurtec ODT (rimegepant) orally disintegrating tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- FDA Approved Drug Products: Nurtec ODT (rimegepant) orally disintegrating tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Quaternary ammonium group transmembrane transporter activity
- Specific Function
- Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- FDA Approved Drug Products: Nurtec ODT (rimegepant) orally disintegrating tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Monovalent cation:proton antiporter activity
- Specific Function
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
- Gene Name
- SLC47A1
- Uniprot ID
- Q96FL8
- Uniprot Name
- Multidrug and toxin extrusion protein 1
- Molecular Weight
- 61921.585 Da
References
- FDA Approved Drug Products: Nurtec ODT (rimegepant) orally disintegrating tablets [Link]
Drug created at October 20, 2016 22:28 / Updated at April 30, 2022 04:55