Ramatroban

Ramatroban
Clinical data

Trade names	Baynas
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral (tablets)
ATC code	None
Legal status
Legal status	Rx-only (JP)
Identifiers
IUPAC name 3-((3R)-3-{[(4-fluorophenyl)sulfonyl]amino}-1,2,3,4-tetrahydro-9H-carbazol-9-yl)propanoic acid
CAS Number	116649-85-5
PubChem (CID)	123879
IUPHAR/BPS	1910
ChemSpider	110413
UNII	P1ALI72U6C^Y
KEGG	D01128
ChEMBL	CHEMBL361812
ECHA InfoCard	100.159.668
Chemical and physical data
Formula	C₂₁H₂₁FN₂O₄S
Molar mass	416.46 g/mol
3D model (Jmol)	Interactive image
SMILES C1CC2=C(CC1NS(=O)(=O)C3=CC=C(C=C3)F)C4=CC=CC=C4N2CCC(=O)O
InChI InChI=1S/C21H21FN2O4S/c22-14-5-8-16(9-6-14)29(27,28)23-15-7-10-20-18(13-15)17-3-1-2-4-19(17)24(20)12-11-21(25)26/h1-6,8-9,15,23H,7,10-13H2,(H,25,26)/t15-/m1/s1 Key:LDXDSHIEDAPSSA-OAHLLOKOSA-N

Ramatroban (INN) is a thromboxane receptor antagonist.^[1]

It is also a DP₂ receptor antagonist.^[2]

It is indicated for the treatment of coronary artery disease.^[3] It has also been used for the treatment of asthma.^[4]

It was developed by the German pharmaceutical company Bayer AG and is co-marketed in Japan by Bayer and Nippon Shinyaku Co. Ltd. under the trade name Baynas.

References

↑ Sugimoto H, Shichijo M, Iino T, et al. (April 2003). "An orally bioavailable small molecule antagonist of CRTH2, ramatroban (BAY u3405), inhibits prostaglandin D2-induced eosinophil migration in vitro". J. Pharmacol. Exp. Ther. 305 (1): 347–52. doi:10.1124/jpet.102.046748. PMID 12649388.
↑ Royer JF, Schratl P, Carrillo JJ, et al. (September 2008). "A novel antagonist of prostaglandin D2 blocks the locomotion of eosinophils and basophils". Eur. J. Clin. Invest. 38 (9): 663–71. doi:10.1111/j.1365-2362.2008.01989.x. PMID 18837743.
↑ Fiedler VB, Seuter F, Perzborn E (December 1990). "Effects of the novel thromboxane antagonist Bay U 3405 on experimental coronary artery disease" (PDF). Stroke. 21 (12 Suppl): IV149–51. PMID 2260140.
↑ Endo S, Akiyama K (November 1996). "[Thromboxane A2 receptor antagonist in asthma therapy]". Nippon Rinsho (in Japanese). 54 (11): 3045–8. PMID 8950952.

External links

(Japanese) Baynas Tablets Prescribing Information

Antithrombotics (thrombolytics, anticoagulants and antiplatelet drugs) (B01)

Antiplatelet drugs

Glycoprotein IIb/IIIa inhibitors	Abciximab Eptifibatide Orbofiban Roxifiban Sibrafiban^§ Tirofiban

ADP receptor/P2Y₁₂ inhibitors	Thienopyridines Clopidogrel Prasugrel Ticlopidine Nucleotide/nucleoside analogs Cangrelor Elinogrel Ticagrelor

Prostaglandin analogue (PGI2)	Beraprost Iloprost Prostacyclin Treprostinil

COX inhibitors	Acetylsalicylic acid/Aspirin^# Aloxiprin Carbasalate calcium Indobufen Triflusal

Thromboxane inhibitors	Thromboxane synthase inhibitors Dipyridamole (+ aspirin) Picotamide Terbogrel Receptor antagonists Terbogrel Terutroban^§

Phosphodiesterase inhibitors	Cilostazol Dipyridamole Triflusal

Other	Cloricromen Ditazole Vorapaxar

Anticoagulants

Vitamin K antagonists
(inhibit II, VII, IX, X)

Factor Xa inhibitors
(with some II inhibition)

Heparin group/ glycosaminoglycans/ (bind antithrombin)	Low molecular weight heparin Bemiparin Certoparin Dalteparin Enoxaparin Nadroparin Parnaparin Reviparin Tinzaparin^‡ Oligosaccharides Fondaparinux Idraparinux^§ Heparinoids Danaparoid Dermatan sulfate Sulodexide

Direct Xa inhibitors ("xabans")	Apixaban Betrixaban^† Darexaban^§ Edoxaban Otamixaban^§ Rivaroxaban

Direct thrombin (IIa) inhibitors

Other

Thrombolytic drugs/
fibrinolytics

Non-medicinal

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Drugs for obstructive airway diseases: asthma/COPD (R03)

Adrenergics, inhalants

Short-acting β₂ agonists	Bitolterol Carbuterol Fenoterol Isoetarine Pirbuterol Procaterol Reproterol Rimiterol Salbutamol (albuterol)^#/Levosalbutamol (levalbuterol) Terbutaline Tulobuterol

Long-acting β₂ agonists	Bambuterol Clenbuterol Formoterol/Arformoterol Salmeterol Salmefamol

Ultra-long-acting β₂ agonists	Abediterol Carmoterol Indacaterol Olodaterol Vilanterol

Other	Epinephrine^# Hexoprenaline Isoprenaline (isoproterenol) Orciprenaline (metaproterenol)

Glucocorticoids

Anticholinergics/
muscarinic antagonist

Mast cell stabilizers

Xanthines

Eicosanoid inhibition

Leukotriene antagonists	Montelukast Pranlukast Zafirlukast

Arachidonate 5-lipoxygenase inhibitors	Zileuton

Thromboxane receptor antagonists	Ramatroban Seratrodast

Non-xanthine PDE4 inhibitors	Ibudilast Roflumilast

Others/unknown

Combination products

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Prostanoid signaling modulators

Receptor
(ligands)

DP (D₂)

DP₁	Agonists: Prostaglandin D₂ Treprostinil Antagonists: Asapiprant Laropiprant Vidupiprant

DP₂	Agonists: Indometacin Prostaglandin D₂ Antagonists: ADC-3680 AZD-1981 Bay U3405 Fevipiprant MK-1029 MK-7246 OC-459 OC000459 QAV-680 Ramatroban Setipiprant TM30089 Vidupiprant

EP (E₂)

EP₁	Agonists: Beraprost Enprostil Iloprost (ciloprost) Latanoprost Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Sulprostone Antagonists: AH-6809 ONO-8130 SC-19220 SC-51089 SC-51322

EP₂	Agonists: Butaprost Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Treprostinil Antagonists: AH-6809 PF-04418948 TG 4-155

EP₃	Agonists: Beraprost Carbacyclin Cicaprost Enprostil Iloprost (ciloprost) Isocarbacyclin Latanoprost Misoprostol Prostaglandin D₂ Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Remiprostol Sulprostone Antagonists: L-798106

EP₄	Agonists: Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) TCS-2510 Antagonists: GW-627368 L-161982 ONO-AE3-208

Unsorted	Agonists: 16,16-Dimethyl Prostaglandin E₂ Aganepag Carboprost Evatanepag Gemeprost Nocloprost Omidenepag Prostaglandin F_2α (dinoprost) Simenepag Taprenepag

FP (F_2α)

IP (I₂)

Agonists: ACT-333679
AFP-07
Beraprost
BMY-45778
Carbacyclin
Cicaprost
Iloprost (ciloprost)
Isocarbacyclin
MRE-269
NS-304
Prostacyclin (prostaglandin I₂, epoprostenol)
Prostaglandin E₁ (alprostadil)
Ralinepag
Selexipag
Taprostene
TRA-418
Treprostinil

Antagonists: RO1138452

TP (TX_A2)

Agonists: Carbocyclic thromboxane A₂
I-BOP
Thromboxane A₂
U-46619
Vapiprost

Antagonists: 12-HETE
13-APA
AA-2414
Argatroban
Bay U3405
BMS-180,291
Daltroban
Domitroban
EP-045
GR-32191
ICI-185282
ICI-192605
Ifetroban
Imitrodast
L-655240
L-670596
Linotroban
Mipitroban
ONO-3708
ONO-11120
Picotamide
Pinane thromboxane A₂
Ramatroban
Ridogrel
S-145
Samixogrel
Seratrodast
SQ-28,668
SQ-29,548
Sulotroban
Terbogrel
Terutroban
TRA-418

Unsorted

Arbaprostil
Ataprost
Ciprostene
Clinprost
Cobiprostone
Delprostenate
Deprostil
Dimoxaprost
Doxaprost
Ecraprost
Eganoprost
Enisoprost
Eptaloprost
Esuberaprost
Etiproston
Fenprostalene
Flunoprost
Froxiprost
Lanproston
Limaprost
Luprostiol
Meteneprost
Mexiprostil
Naxaprostene
Nileprost
Nocloprost
Ornoprostil
Oxoprostol
Penprostene
Pimilprost
Piriprost
Posaraprost
Prostalene
Rioprostil
Rivenprost
Rosaprostol
Spiriprostil
Tiaprost
Tilsuprost
Tiprostanide
Trimoprostil
Viprostol

Enzyme
(inhibitors)

COX (PTGS)	Aceclofenac Acemetacin Acetanilide Alclofenac Alminoprofen Aloxiprin AM404 Amfenac Ampiroxicam Anitrazafen Antrafenine Apricoxib Aspirin (acetylsalicylic acid) Azapropazone Bendazac Benorilate (benorylate) Benoxaprofen Bromfenac Bucetin Bucloxic acid (blucloxate) Bufexamac Bumadizone Butibufen Carbasalate calcium Carprofen Celecoxib Cimicoxib Cinmetacin Clobuzarit Clometacin Clonixeril Clonixin Curcumin Deracoxib Dexibuprofen Dexindoprofen Dexketoprofen Diclofenac Difenpiramide Diflunisal Dipyrocetyl Droxicam DuP-697 Enolicam Ethenzamide Etodolac Etofenamate Etoricoxib Felbinac Fenbufen Fenclofenac Fenoprofen Fentiazac Firocoxib FK-3311 Floctafenic acid (floctafenate) Floctafenine Flosulide Flufenamic acid (flufenamate) Flumizole Flunixin Flunoxaprofen Fluproquazone Flurbiprofen FR-122047 Glafenine Glimepiride Glucametacin Guacetisal Hyperforin Ibuprofen Ibuproxam Indometacin farnesil Indometacin (indomethacin) Indoprofen Isoxicam Itazigrel Ketoprofen Ketorolac L-655240 L-670596 Licofelone Lonazolac Lornoxicam Loxoprofen Lumiracoxib Magnesium salicylate Mavacoxib Meclofenamic acid (meclofenamate) Mefenamic acid (mefenamate) Meloxicam Menatetrenone (vitamin K₂) Mesalazine (5-aminosalicylic acid) Methyl salicylate Miroprofen Mofezolac Morniflumate Nabumetone Naproxcinod Naproxen NCX-466 NCX-4040 Niflumic acid (niflumate) Nimesulide NS-398 Oxametacin Oxaprozin Oxindanac Pamicogrel Paracetamol (acetaminophen) Parapropamol Parecoxib Phenacetin Piroxicam Pirprofen Polmacoxib Pranoprofen Proglumetacin Propacetamol Resveratrol Robenacoxib Rofecoxib Romazarit Rutecarpine Salacetamide Salicin Salicylamide Salicylic acid (salicylate) Salsalate Satigrel SC-236 SC-560 SC-58125 Sodium salicylate Sulindac Sulindac sulfide Suprofen Talinflumic acid (talinflumate) Tarenflurbil Tenidap Tenoxicam Tepoxalin Tiaprofenic acid (tiaprofenate) Tiflamizole Tilmacoxib Timegadine Tolfenamic acid (tolfenamate) Tolmetin Trifenagrel Triflusal Tropesin Valdecoxib Vedaprofen Zidometacin Zomepirac

PGD₂ synthase	Retinoids Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)

PGE synthase	HQL-79

PGF synthase	Bimatoprost

PGI₂ synthase	Tranylcypromine

TXA synthase	Camonagrel Dazmegrel Dazoxiben Furegrelate Isbogrel Midazogrel Nafagrel Nicogrelate Ozagrel Picotamide Pirmagrel Ridogrel Rolafagrel Samixogrel Terbogrel U63557A

Others

See also: Leukotrienergics

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