Acefylline

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Acefylline

Molecular FormulaC₉H₁₀N₄O₄
Average mass238.200 Da

(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)acetic acid

1,2,3,6-Tetrahydro-1,3-dimethyl-2,6-dioxo-7H-purine-7-acetic Acid

1,3-Dimethylxanthine-7-acetic acid

211-490-2 [EINECS]

652-37-9 [RN]

7-(Carboxymethyl)theophylline

7H-Purine-7-acetic acid, 1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-

CAS Registry Number: 652-37-9

CAS Name: 1,2,3,6-Tetrahydro-1,3-dimethyl-2,6-dioxopurine-7-acetic acid

Additional Names: carboxymethyltheophylline; 7-theophyllineacetic acid

Molecular Formula: C9H10N4O4

Molecular Weight: 238.20

Percent Composition: C 45.38%, H 4.23%, N 23.52%, O 26.87%

Literature References: Prepn: DE 352980 (1922 to E. Merck); Frdl. 14, 1320; S. M. Ride et al., Pharmazie 32, 672 (1977). Prepn of salts: J. Baisse, Bull. Soc. Chim. Fr. 1949, 769; M. Milletti, F. Virgili, Chimica 6, 394 (1951), C.A. 46, 8615h (1952). GC determn in urine: J. Zuidema, H. Hilbers, J. Chromatogr. 182, 445 (1980). HPLC determn in serum and pharmacokinetics: S. Sved et al.,Biopharm. Drug Dispos. 2, 177 (1981).

Properties: Crystals from water, mp 271°.

Melting point: mp 271°

Derivative Type: Sodium salt

CAS Registry Number: 837-27-4

Molecular Formula: C9H9N4NaO4

Molecular Weight: 260.18

Percent Composition: C 41.55%, H 3.49%, N 21.53%, Na 8.84%, O 24.60%

Properties: Silky needles, mp >300°.

Melting point: mp >300°

Derivative Type: Compd with piperazine

Additional Names: Acefylline piperazine; acepifylline

Trademarks: Dynaphylline (Welcker-Lyster); Etaphylline (Delalande); Etafillina (Delalande)

Properties: Undefined mixture of the 1:1 and 2:1 salts; contains 75-78% theophylline acetic acid and 22-25% anhydrous piperazine.

Therap-Cat: Bronchodilator.

Keywords: Bronchodilator; Xanthine Derivatives.

Acefylline (INN),^[1] also known as acetyloxytheophylline, is a stimulant drug of the xanthine chemical class. It acts as an adenosine receptor antagonist. It is combined with diphenhydramine in the pharmaceutical preparation etanautine to help offset diphenhydramine induced drowsiness.^[2]

Synthesis

DE 352980 (1922 to E. Merck); Frdl. 14, 1320; S. M. Ride et al., Pharmazie 32, 672 (1977).

Acefylline

Use:cardiotonic, diuretic, antispasmodic, bronchodilator

Chemical name:1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-7H-purine-7-acetic acid

Formula:C₉H₁₀N₄O₄

MW:238.20 g/mol
CAS-RN:652-37-9
EINECS:211-490-2
LD₅₀:1180 mg/kg (M, i.p.); 2733 mg/kg (M, p.o.)

Acepifylline

Use:

Chemical name:1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-7H-purine-7-acetic acid compd. with piperazine

Formula:C₉H₁₀N₄O₄ • xC₄H₁₀N₂

MW:unspecified
CAS-RN:18833-13-1
EINECS:242-614-3

Acefylline heptaminol

Use:

Chemical name:1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-7H-purine-7-acetic acid compd. with 6-amino-2-methyl-2-heptaminol (1:1)

Formula:C₉H₁₀N₄O₃ • C₈H₁₉NO

MW:367.45 g/mol
CAS-RN:59989-20-7
EINECS:262-012-4

References

^ “International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names (Rec. INN): List 21” (PDF). World Health Organization. Retrieved 29 December 2016.
^ Zuidema, Jan. (1978). “Biofarmaceutische en farmacokinetische aspecten van theofylline en acefylline”. Thesis (doctoral)–Universiteit van Amsterdam. References

Baisse, J.: Bull. Soc. Chim. Fr. (BSCFAS) 1949, 769.

DE 352 980 (E. Merck; 1922).

Acefylline
Clinical data


ATC code	R03DA09 (WHO) (acefylline piperazine)
Identifiers
IUPAC name [show]
CAS Number	652-37-9
PubChemCID	69550
ChemSpider	62754
UNII	M494UE2YEP
ChEMBL	ChEMBL70246
ECHA InfoCard	100.010.447
Chemical and physical data
Formula	C₉H₁₀N₄O₄
Molar mass	238.20 g/mol g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES [hide] O=C2N(c1ncn(c1C(=O)N2C)CC(=O)O)C
InChI [hide] InChI=1S/C9H10N4O4/c1-11-7-6(8(16)12(2)9(11)17)13(4-10-7)3-5(14)15/h4H,3H2,1-2H3,(H,14,15) Key:HCYFGRCYSCXKNQ-UHFFFAOYSA-N

////////Acefylline

It's only fair to share...

Acefylline

Acepifylline

Acefylline heptaminol

References

Baisse, J.: Bull. Soc. Chim. Fr. (BSCFAS) 1949, 769.

DE 352 980 (E. Merck; 1922).

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