Enprofylline

Enprofylline
Identifiers

IUPAC name 3-propyl-7H-purine-2,6-dione
CAS Number	41078-02-8^Y
PubChem (CID)	1676
DrugBank	DB00824^N
ChemSpider	1613^Y
UNII	DT7DT5E518^N
ChEBI	CHEBI:126237^N
ChEMBL	CHEMBL279898^N
ECHA InfoCard	100.050.166
Chemical and physical data
Formula	C₈H₁₀N₄O₂
Molar mass	194.190 g/mol
3D model (Jmol)	Interactive image
SMILES O=C2N(c1ncnc1C(=O)N2)CCC
InChI InChI=1S/C8H10N4O2/c1-2-3-12-6-5(9-4-10-6)7(13)11-8(12)14/h4H,2-3H2,1H3,(H,9,10)(H,11,13,14)^Y Key:SIQPXVQCUCHWDI-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Enprofylline (3-Propylxanthine) is a xanthine derivative used in the treatment of asthma, which acts as a bronchodilator. It acts primarily as a competitive nonselective phosphodiesterase inhibitor with relatively little activity as a nonselective adenosine receptor antagonist.^[1]^[2]

References

↑ Lunell E, Svedmyr N, Andersson KE, Persson CG (1982). "Effects of enprofylline, a xanthine lacking adenosine receptor antagonism, in patients with chronic obstructive lung disease". European Journal of Clinical Pharmacology. 22 (5): 395–402. doi:10.1007/bf00542541. PMID 6288396.
↑ Laursen LC (December 1987). "Anti asthmatic effects and pharmacokinetics of enprofylline--a new xanthine derivate". Danish Medical Bulletin. 34 (6): 289–97. PMID 3325233.

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^‡Withdrawn from market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

PDE inhibitors

PDE1	MMPX SCH-51866 Vinpocetine

PDE2	BAY 60-7550 EHNA Oxindole PDP

PDE3	Adibendan Amrinone (inamrinone) Anagrelide Bucladesine Cilostamide Cilostazol Enoximone Imazodan KMUP-1 Meribendan Milrinone Olprinone Parogrelil Pimobendan Quazinone RPL-554 Siguazodan Tetomilast Tofimilast Trequinsin Vesnarinone

PDE4	Apremilast Arofylline Atizoram Catramilast CC-1088 CDP-840 CGH-2466 Cilomilast Cipamfylline CP-80633 Crisaborole Denbutylline Drotaverine Etazolate Filaminast Glaucine HT-0712 ICI-63197 Indimilast Irsogladine Lavamilast Lirimilast Luteolin Mesembrenone Mesembrine Mesopram Oglemilast Piclamilast Revamilast Ro 20-1724 Roflumilast Rolipram Ronomilast RPL-554 RS-25344 YM-976

PDE5	Acetildenafil Aildenafil Avanafil Beminafil Benzamidenafil Dasantafil Icariin Gisadenafil Homosildenafil Lodenafil Mirodenafil MY-5445 Nitrosoprodenafil Sildenafil Sulfoaildenafil T-0156 Tadalafil Udenafil Vardenafil

PDE7	BRL-50481

PDE9	BAY 73-6691 PF-04447943

PDE10	Papaverine PF-2545920 TC-E 5005 Tofisopam

PDE11	BC11-38

Non-selective	Aminophylline Caffeine Choline theophyllinate CPX Dipyridamole Doxofylline Enprofylline Ibudilast IBMX Luteolin Paraxanthine Pentoxifylline Propentofylline SCH-51866 Theobromine Theophylline Zaprinast Zardaverine

Unsorted	Benafentrine Carbazeran Diazepam Diphylline Doxofylline DPCPX Furafylline Lisofylline MDL-12330A Moxaverine Oxagrelate Pentifylline Proxyphylline Pumafentrine Quercetin Satigrel Tolafentrine Trapidil

Purinergics

Receptor
(ligands)

P0
(adenine)

Agonists: 8-Aminoadenine
Adenine

P1
(adenosine)

Agonists: 2-(1-Hexynyl)-N-methyladenosine
2-Cl-IB-MECA
2'-MeCCPA
4'-O-β-D-Glucosyl-9-O-(6''-deoxysaccharosyl)olivil
5'-N-ethylcarboxamidoadenosine
Adenosine
ADP
AMP
Apadenoson
ATL-146e
ATP
BAY 60–6583
Binodenoson
Capadenoson
CCPA
CGS-21680
CP-532,903
Evodenoson
GR 79236
LUF-5835
LUF-5845
N⁶-Cyclopentyladenosine
Neladenoson dalanate
Piclidenoson
Regadenoson
SDZ WAG 994
Selodenoson
Sonedenoson
Tecadenoson
UK-432,097

P2
(nucleotide)

P2X (ATP)	Agonists: 2-Me-SATP α,β-Me-ATP Adenosine ADP AMP Ap4A Ap5A ATP ATPγS BzATP Cibacron blue CTP D-β,γ-Me-ATP GTP HT-AMP Ivermectin L-β,γ-Me-ATP MRS-2219 PAPET-ATP UTP Zinc Antagonists: 5-BDBD A-317491 A-438079 A-740003 A-804598 A-839977 AF-353 AZ-10606120 AZ-11645373 BBG Calcium Calmidazolium Chelerythrine Copper Emodin (Rheum officinale) Evans Blue GW-791343 HMA Ip5I isoPPADS JNJ-47965567 KN-04 KN-62 Magnesium MRS-2159 NF-023 NF-110 NF-157 NF-279 NF-449 Oxidized-ATP Phenol Red Phenolphthalein PPADS PPNDS PSB-12062 Puerarin (Radix puerariae) Purotoxin 1 RB-2 Ro 0437626 Ro 51 RO-3 Sodium ferulate (Angelica sinensis, Ligusticum wallichii) Suramin TC-P 262 Tetramethylpyrazine (ligustrazine) (Ligusticum wallichii) TNP-ATP Zinc

P2Y	Agonists: 2-Me-SADP 2-Me-SATP 2-Thio-UTP 5-Br-UDP 5-OMe-UDP α,β-Me-ATP Adenosine ADP ADPβS Ap3A AR-C 67085MX ATP ATPγS CTP dATP Denufosol Diquafosol IDP ITP INS-365 INS-37217 MRS-2365 MRS-2690 MRS-2693 MRS-2768 MRS-2957 MRS-4062 NF-546 PAPET-ATP PSB-0474 PSB-1114 UDP UDPβS UDP-galactose UDP-glucose UDP-N-acetylglucosamine Up3U UTP UTPγS Antagonists: 2-Me-SAMP A3P5PS AMPαS Ap4A AR-C 66096 AR-C 67085MX AR-C 69931MX AR-C 118925XX ATP BzATP C1330-7 Cangrelor Clopidrogel Elinogrel Ip5I MRS-2179 MRS-2211 MRS-2279 MRS-2395 MRS-2500 MRS-2578 NF-157 NF-340 PIT PPADS Prasugrel PSB-0739 RB-2 Regrelor Suramin Ticagrelor Ticlopidine UDP

Transporter
(blockers)

CNTs	6-Hydroxy-7-methoxyflavone Adenosine dMeThPmR Estradiol KGO-2142 KGO-2173 MeThPmR Phloridzin Progesterone

ENTs	Barbiturates Benzodiazepines Cilostazol Dilazep Dipyridamole Estradiol Ethanol Hexobendine NBMPR Pentoxifylline Progesterone Propentofylline

PMAT	Decynium-22

Enzyme
(inhibitors)

XO	Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol Myricetin Niraxostat Oxypurinol Phytic acid Pistacia integerrima Propolis Quercetin Tisopurine Topiroxostat

Others	Aminopterin Azathioprine Methotrexate Mycophenolic acid Pemetrexed Pralatrexate Many others

Others

Others: Chrysophanol (rhubarb)

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